CH378316A - Verfahren zur Herstellung von substituierten 2,4-Dioxo-tetrahydropyridinen - Google Patents

Verfahren zur Herstellung von substituierten 2,4-Dioxo-tetrahydropyridinen

Info

Publication number: CH378316A
Authority: CH; Switzerland
Prior art keywords: substituted; dioxo; acid ester; acetylacetamide; carboxylic acid
Prior art date: 1959-02-06

Application number

CH6920759A

Other languages

German (de)

English (en)

Inventor

Rudolf Dr Hinderling

Hans Dr Lutz August

Otto Dr Schnider

Original Assignee

Hoffmann La Roche

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.)

1959-02-06

Filing date

1959-02-06

Publication date

1964-06-15

1959-02-06 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1959-02-06 Priority to CH6920759A priority Critical patent/CH378316A/de

1960-01-27 Priority to BE586987A priority patent/BE586987A/fr

1964-06-15 Publication of CH378316A publication Critical patent/CH378316A/de

Links

238000000034 method Methods 0.000 title claims description 10
RDNZDMDLRIQQAX-UHFFFAOYSA-N piperidine-2,4-dione Chemical class O=C1CCNC(=O)C1 RDNZDMDLRIQQAX-UHFFFAOYSA-N 0.000 title claims description 8
238000002360 preparation method Methods 0.000 title claims description 4
GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical compound CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 claims description 7
150000001733 carboxylic acid esters Chemical class 0.000 claims description 7
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 7
-1 alkali metal salts Chemical class 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 6
229910052783 alkali metal Inorganic materials 0.000 claims description 5
150000001875 compounds Chemical class 0.000 claims description 5
239000000725 suspension Substances 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000000547 substituted alkyl group Chemical group 0.000 claims description 4
238000009833 condensation Methods 0.000 claims description 3
230000005494 condensation Effects 0.000 claims description 3
235000019253 formic acid Nutrition 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 3
239000007858 starting material Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
238000002844 melting Methods 0.000 description 4
TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
WUVXRNGXQRVRLV-UHFFFAOYSA-N pyridine-2,3-dione Chemical compound O=C1C=CC=NC1=O WUVXRNGXQRVRLV-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
239000012670 alkaline solution Substances 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
NZASCBIBXNPDMH-UHFFFAOYSA-N 3,3-diethyl-1H-pyridine-2,4-dione Chemical compound CCC1(CC)C(=O)NC=CC1=O NZASCBIBXNPDMH-UHFFFAOYSA-N 0.000 description 1
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 1
ZKBIYSGYULIHER-UHFFFAOYSA-N 6-methyl-3,3-dipropylpiperidine-2,4-dione Chemical compound C(CC)C1(C(NC(CC1=O)C)=O)CCC ZKBIYSGYULIHER-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
QPDBJOGQOPKDGK-UHFFFAOYSA-N C(C)(C)C1C(NCCC1=O)=O Chemical compound C(C)(C)C1C(NCCC1=O)=O QPDBJOGQOPKDGK-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000002082 anti-convulsion Effects 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
150000001559 benzoic acids Chemical class 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000000147 hypnotic effect Effects 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000155 melt Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000000203 mixture Substances 0.000 description 1
ZSBDPRIWBYHIAF-UHFFFAOYSA-N n-acetylacetamide Chemical class CC(=O)NC(C)=O ZSBDPRIWBYHIAF-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
150000003901 oxalic acid esters Chemical class 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000012485 toluene extract Substances 0.000 description 1

Landscapes

Pyridine Compounds (AREA)
Hydrogenated Pyridines (AREA)

CH6920759A 1959-02-06 1959-02-06 Verfahren zur Herstellung von substituierten 2,4-Dioxo-tetrahydropyridinen CH378316A (de)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
CH6920759A CH378316A (de)	1959-02-06	1959-02-06	Verfahren zur Herstellung von substituierten 2,4-Dioxo-tetrahydropyridinen
BE586987A BE586987A (fr)	1959-02-06	1960-01-27	Procédé pour la préparation de 2,4-dioxotétrahydropyridines substituées.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH6920759A CH378316A (de)	1959-02-06	1959-02-06	Verfahren zur Herstellung von substituierten 2,4-Dioxo-tetrahydropyridinen

Publications (1)

Publication Number	Publication Date
CH378316A true CH378316A (de)	1964-06-15

Family

ID=4529324

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH6920759A CH378316A (de)	1959-02-06	1959-02-06	Verfahren zur Herstellung von substituierten 2,4-Dioxo-tetrahydropyridinen

Country Status (2)

Country	Link
BE (1)	BE586987A (fr)
CH (1)	CH378316A (fr)

1959
- 1959-02-06 CH CH6920759A patent/CH378316A/de unknown
1960
- 1960-01-27 BE BE586987A patent/BE586987A/fr unknown

Also Published As

Publication number	Publication date
BE586987A (fr)	1960-07-27

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DE1493854B1 (de)	1971-05-27	Benzanilide und Verfahren zu ihrer Herstellung
DE1162841B (de)	1964-02-13	Verfahren zur Herstellung von Dihydro-1, 3, 5-dithiazinverbindungen
CH378316A (de)	1964-06-15	Verfahren zur Herstellung von substituierten 2,4-Dioxo-tetrahydropyridinen
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AT214920B (de)	1961-05-10	Verfahren zur Herstellung von substituierten 2,4-Dioxo-tetra-hydropyridinen
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DE1493854C (de)	1971-12-30	Benzanilide und Verfahren zu ihrer Herstellung
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DE1445482C (de)	1971-09-23	4 (3H)-Pyrimidone und Verfahren zu deren Herstellung
DE1067028B (fr)	1959-10-15
DE1047788B (de)	1958-12-31	Verfahren zur Herstellung von Derivaten des 4-Oxycumarins
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AT228407B (de)	1963-07-10	Verfahren zur Herstellung neuer Ester von N-(Hydroxyalkyl)-nortropanen bzw. -norgranatanen, deren Salzen und quartären Ammoniumverbindungen
AT227696B (de)	1963-06-10	Verfahren zur Herstellung von 2-Amino-oxazolen
DE825548C (de)	1951-12-20	Verfahren zur Herstellung von neuen diquartaeren Salzen von Pyrimidylaminocinnolinen
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