NO323397B1 - Fremgangsmate for fremstilling av quinolylakrylonitril og intermediater derfor - Google Patents

Fremgangsmate for fremstilling av quinolylakrylonitril og intermediater derfor Download PDF

Info

Publication number: NO323397B1
Authority: NO; Norway
Prior art keywords: cyclopropyl; fluorophenyl; carbaldehyde; base; prop
Prior art date: 2000-01-24

Application number

NO20023505A

Other languages

English (en)

Norwegian (no)

Other versions

NO20023505D0 (no

NO20023505L (no

Inventor

Katsumasa Harada

Shigeyoshi Nishino

Naoko Okada

Hidetaka Shima

Takashi Harada

Original Assignee

Nissan Chemical Ind Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2000-01-24

Filing date

2002-07-23

Publication date

2007-04-23

2002-07-23 Application filed by Nissan Chemical Ind Ltd filed Critical Nissan Chemical Ind Ltd

2002-07-23 Publication of NO20023505D0 publication Critical patent/NO20023505D0/no

2002-09-05 Publication of NO20023505L publication Critical patent/NO20023505L/no

2007-04-23 Publication of NO323397B1 publication Critical patent/NO323397B1/no

Links

238000000034 method Methods 0.000 title claims description 31
238000002360 preparation method Methods 0.000 title claims description 11
239000000543 intermediate Substances 0.000 title 1
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 66
238000006243 chemical reaction Methods 0.000 claims abstract description 21
239000003960 organic solvent Substances 0.000 claims abstract description 14
JAHBIRPTCXOGLB-UHFFFAOYSA-N 2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-carbaldehyde Chemical compound C1=CC(F)=CC=C1C1=C(C=O)C(C2CC2)=NC2=CC=CC=C12 JAHBIRPTCXOGLB-UHFFFAOYSA-N 0.000 claims abstract description 12
239000000203 mixture Substances 0.000 claims description 28
OSKJUNDAPNVBMM-UHFFFAOYSA-N 2-cyclopropyl-4-(4-fluorophenyl)-3-prop-1-enylquinoline;nitrous acid Chemical compound ON=O.CC=CC1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1 OSKJUNDAPNVBMM-UHFFFAOYSA-N 0.000 claims description 20
-1 organic acid ester Chemical class 0.000 claims description 15
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 13
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 12
239000012024 dehydrating agents‎ Substances 0.000 claims description 11
229910052751 metal Inorganic materials 0.000 claims description 8
239000002184 metal Substances 0.000 claims description 8
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical group [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
239000012312 sodium hydride Substances 0.000 claims description 7
229910000104 sodium hydride Inorganic materials 0.000 claims description 7
150000004703 alkoxides Chemical class 0.000 claims description 6
150000001408 amides Chemical class 0.000 claims description 6
235000019253 formic acid Nutrition 0.000 claims description 6
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 5
229910052987 metal hydride Inorganic materials 0.000 claims description 5
150000004681 metal hydrides Chemical class 0.000 claims description 5
150000007524 organic acids Chemical class 0.000 claims description 5
239000003849 aromatic solvent Substances 0.000 claims description 4
229910000000 metal hydroxide Inorganic materials 0.000 claims description 4
150000004692 metal hydroxides Chemical class 0.000 claims description 4
150000003512 tertiary amines Chemical class 0.000 claims description 4
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 3
AJXPQJBVTAQBRE-UHFFFAOYSA-N 3-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3-hydroxypropanenitrile Chemical compound N#CCC(O)C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1 AJXPQJBVTAQBRE-UHFFFAOYSA-N 0.000 claims description 3
CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 claims description 3
150000001875 compounds Chemical class 0.000 claims description 3
150000007522 mineralic acids Chemical group 0.000 claims description 3
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 claims description 3
229910000105 potassium hydride Inorganic materials 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 3
239000002585 base Substances 0.000 claims 9
GPWNWKWQOLEVEQ-UHFFFAOYSA-N 2,4-diaminopyrimidine-5-carbaldehyde Chemical compound NC1=NC=C(C=O)C(N)=N1 GPWNWKWQOLEVEQ-UHFFFAOYSA-N 0.000 claims 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
229910000077 silane Inorganic materials 0.000 claims 2
229910052783 alkali metal Inorganic materials 0.000 claims 1
150000001340 alkali metals Chemical class 0.000 claims 1
229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
150000001342 alkaline earth metals Chemical class 0.000 claims 1
230000018044 dehydration Effects 0.000 abstract 1
238000006297 dehydration reaction Methods 0.000 abstract 1
239000011541 reaction mixture Substances 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
239000012074 organic phase Substances 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
WPYJKGWLDJECQD-UHFFFAOYSA-N quinoline-2-carbaldehyde Chemical class C1=CC=CC2=NC(C=O)=CC=C21 WPYJKGWLDJECQD-UHFFFAOYSA-N 0.000 description 10
239000007858 starting material Substances 0.000 description 10
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
238000004128 high performance liquid chromatography Methods 0.000 description 8
239000000047 product Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000011521 glass Substances 0.000 description 6
238000004445 quantitative analysis Methods 0.000 description 6
229920006395 saturated elastomer Polymers 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
239000011780 sodium chloride Substances 0.000 description 5
238000005160 1H NMR spectroscopy Methods 0.000 description 4
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000007787 solid Substances 0.000 description 4
WULPWIFGZFQFEQ-UHFFFAOYSA-N 3-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]prop-2-enal Chemical compound C1=CC(F)=CC=C1C1=C(C=CC=O)C(C2CC2)=NC2=CC=CC=C12 WULPWIFGZFQFEQ-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 3
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
238000000262 chemical ionisation mass spectrometry Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 3
239000013067 intermediate product Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
238000005406 washing Methods 0.000 description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
HGINCPLSRVDWNT-UHFFFAOYSA-N acrylaldehyde Natural products C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
239000012300 argon atmosphere Substances 0.000 description 2
NMJJFJNHVMGPGM-UHFFFAOYSA-N butyl formate Chemical compound CCCCOC=O NMJJFJNHVMGPGM-UHFFFAOYSA-N 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 2
238000002451 electron ionisation mass spectrometry Methods 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
239000004210 ether based solvent Substances 0.000 description 2
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
WRXZCLBKDXISQA-UHFFFAOYSA-N 2-chloro-7-methoxyquinoline-3-carbaldehyde Chemical class C1=C(C=O)C(Cl)=NC2=CC(OC)=CC=C21 WRXZCLBKDXISQA-UHFFFAOYSA-N 0.000 description 1
JFVAZAQELKYEFZ-UHFFFAOYSA-N 2-cyclopropyl-4-(4-fluorophenyl)quinoline Chemical compound C1=CC(F)=CC=C1C1=CC(C2CC2)=NC2=CC=CC=C12 JFVAZAQELKYEFZ-UHFFFAOYSA-N 0.000 description 1
RVDLHGSZWAELAU-UHFFFAOYSA-N 5-tert-butylthiophene-2-carbonyl chloride Chemical compound CC(C)(C)C1=CC=C(C(Cl)=O)S1 RVDLHGSZWAELAU-UHFFFAOYSA-N 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 1
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
239000012156 elution solvent Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
HQVFCQRVQFYGRJ-UHFFFAOYSA-N formic acid;hydrate Chemical compound O.OC=O HQVFCQRVQFYGRJ-UHFFFAOYSA-N 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
229910000103 lithium hydride Inorganic materials 0.000 description 1
UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
ULWOJODHECIZAU-UHFFFAOYSA-N n,n-diethylpropan-2-amine Chemical compound CCN(CC)C(C)C ULWOJODHECIZAU-UHFFFAOYSA-N 0.000 description 1
150000002815 nickel Chemical group 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
QPHVQMSISUVMAP-UHFFFAOYSA-N prop-2-enoic acid;quinoline Chemical compound OC(=O)C=C.N1=CC=CC2=CC=CC=C21 QPHVQMSISUVMAP-UHFFFAOYSA-N 0.000 description 1
RYGIHSLRMNXWCN-UHFFFAOYSA-N quinoline-3-carbaldehyde Chemical compound C1=CC=CC2=CC(C=O)=CN=C21 RYGIHSLRMNXWCN-UHFFFAOYSA-N 0.000 description 1
150000004756 silanes Chemical class 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Quinoline Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

NO20023505A 2000-01-24 2002-07-23 Fremgangsmate for fremstilling av quinolylakrylonitril og intermediater derfor NO323397B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP2000014864A JP4496586B2 (ja)	2000-01-24	2000-01-24	キノリルアクリロニトリルの製造法及びその中間体
PCT/JP2001/000451 WO2001053264A1 (en)	2000-01-24	2001-01-24	Process for preparing quinolylacrylonitrile and intermediates therefor

Publications (3)

Publication Number	Publication Date
NO20023505D0 NO20023505D0 (no)	2002-07-23
NO20023505L NO20023505L (no)	2002-09-05
NO323397B1 true NO323397B1 (no)	2007-04-23

Family

ID=18542251

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20023505A NO323397B1 (no)	2000-01-24	2002-07-23	Fremgangsmate for fremstilling av quinolylakrylonitril og intermediater derfor

Country Status (25)

Country	Link
US (1)	US6541636B2 (de)
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JP (1)	JP4496586B2 (de)
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CN (1)	CN1179946C (de)
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HU (1)	HU230001B1 (de)
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MX (1)	MXPA02007182A (de)
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UA (1)	UA72025C2 (de)
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US7223428B2 (en) *	1998-01-09	2007-05-29	Mars Incorporated	Method of embossing chocolate products
JP2002155056A (ja) *	2000-11-17	2002-05-28	Ube Ind Ltd	キノリルアクリロニトリル誘導体の製法
US20050182125A1 (en) *	2003-05-16	2005-08-18	Ambit Biosciences Corporation	Pyrrole compounds and uses thereof
WO2004110998A1 (en) *	2003-05-16	2004-12-23	Ambit Biosciences Corporation	Pyrrole compounds and uses thereof
US20040248972A1 (en) *	2003-05-16	2004-12-09	Ambit Biosciences Corporation	Compounds and uses thereof
CA2542182A1 (en) *	2003-10-09	2005-04-28	Ecole Polytechnique Federale De Lausanne	Method for identification of suitable fragmentation sites in a reporter protein
BRPI0719449A2 (pt)	2006-12-21	2017-06-20	Syngenta Participations Ag	molécula de ácido nucléico isolada, sintética ou recombinante, polipeptídeo isolado, planta ou parte de planta, eículo de clonagem que compreende um ácido nucléico, cassete de expressão que compreende uma molécula de ácido nucléico e método para hidrolisar um polissacarídeo, oligossacarídeo ou amido
CN102106941B (zh) *	2011-01-30	2012-05-30	广西柳州今传古草生物科技有限公司	治疗痔疮的中药制剂及其制备方法

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JP2569746B2 (ja) *	1987-08-20	1997-01-08	日産化学工業株式会社	キノリン系メバロノラクトン類
US5008270A (en) *	1989-10-31	1991-04-16	Biocryst, Inc.	2-amino-7-(heterocyclomethyl)-3H,5H-pyrrolo[3,2-d]pyrimidin-4-ones and pharmaceutical uses and compositions containing the same
AU654264B2 (en) *	1989-10-31	1994-11-03	Biocryst Pharmaceuticals, Inc.	Inhibitors of purine nucleoside phosphorylase
US5286721A (en) *	1990-10-15	1994-02-15	Fujisawa Pharmaceutical Co., Ltd.	1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid compounds
JP3130342B2 (ja) *	1991-10-04	2001-01-31	日産化学工業株式会社	動脈硬化性血管内膜肥厚抑制薬
US5710164A (en) *	1995-06-06	1998-01-20	American Home Products Corporation	Diheterocyclic styryl nitriles
US6335449B1 (en) *	1998-07-23	2002-01-01	Nissan Chemical Industries, Ltd.	Process for the preparation of quinoline derivative and intermediate therefor

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ZA200205849B (en)	2003-10-22
DE60104394D1 (de)	2004-08-26
RU2002122754A (ru)	2004-01-10
SI1251123T1 (en)	2004-10-31
HUP0204145A3 (en)	2005-05-30
HUP0204145A2 (hu)	2003-03-28
KR100578776B1 (ko)	2006-05-12
EP1251123A1 (de)	2002-10-23
ES2220705T3 (es)	2004-12-16
NO20023505D0 (no)	2002-07-23
PT1251123E (pt)	2004-11-30
ATE271545T1 (de)	2004-08-15
EP1251123A4 (de)	2003-02-05
RU2260000C2 (ru)	2005-09-10
WO2001053264A1 (en)	2001-07-26
JP2001199962A (ja)	2001-07-24
IL150881A0 (en)	2003-02-12
CZ301252B6 (cs)	2009-12-23
NZ520415A (en)	2003-09-26
CA2398113A1 (en)	2001-07-26
KR20020084099A (ko)	2002-11-04
EP1251123B1 (de)	2004-07-21
SK10812002A3 (sk)	2003-03-04
MXPA02007182A (es)	2003-11-25
JP4496586B2 (ja)	2010-07-07
CN1179946C (zh)	2004-12-15
TR200401864T4 (tr)	2004-08-23
CN1419543A (zh)	2003-05-21
US6541636B2 (en)	2003-04-01
IL150881A (en)	2008-07-08
UA72025C2 (uk)	2005-01-17
DK1251123T3 (da)	2004-11-22
HU230001B1 (en)	2015-04-28
SK286905B6 (sk)	2009-07-06
AU2709901A (en)	2001-07-31
NO20023505L (no)	2002-09-05
AU777959B2 (en)	2004-11-04
US20030013885A1 (en)	2003-01-16
DE60104394T2 (de)	2005-08-18
CA2398113C (en)	2010-01-05

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RU2260000C2 (ru)	2005-09-10	Способ получения хинолилакрилонитрила и соответствующих промежуточных продуктов
KR960001913B1 (ko)	1996-02-06	3-시아노-4-아릴-피롤의 제조방법
JP2001199962A5 (de)	2006-11-30
JP3452081B2 (ja)	2003-09-29	フルオロ−トリフルオロメチル安息香酸誘導体類
EP1361215B1 (de)	2012-03-21	Verfahren zur herstellung von chinolincarboxaldehydderivaten und deren zwischenprodukte
CZ304984B6 (cs)	2015-03-11	Zlepšený způsob výroby a nové intermediáty syntézy elvitegraviru
CN110563696A (zh)	2019-12-13	含杂原子环己烯卤代物的制备方法
KR950003333B1 (ko)	1995-04-10	α,β-불포화케톤 및 케토옥심유도체
US5633380A (en)	1997-05-27	Substituted quinoline herbicide intermediates and process
CA2398138C (en)	2009-12-22	Process for the preparation of quinolylpropenal
JP4690733B2 (ja)	2011-06-01	３−ヒドロキシピラゾール−１−カルボキサミド誘導体の製造方法
WO2009119086A1 (ja)	2009-10-01	９－ヒドロキシメチル－シクロヘプタ［ｂ］ピリジン－３－カルボン酸エステル誘導体の製造方法
JP2002155056A (ja)	2002-05-28	キノリルアクリロニトリル誘導体の製法
JP2002322153A (ja)	2002-11-08	キノリンカルボン酸エステル誘導体又はそのスルホン酸塩の製造法
JP2001199964A (ja)	2001-07-24	キノリルプロペナールの製造方法
JP2002187883A (ja)	2002-07-05	６−（１−フルオロエチル）−５−ヨード−４−ピリミドン及びその製法