DD234574A3 - Verfahren zur herstellung von 3-amino-5-(pyrid-4-yl)-1,2-dihydro-pyrid-2-on - Google Patents

Verfahren zur herstellung von 3-amino-5-(pyrid-4-yl)-1,2-dihydro-pyrid-2-on Download PDF

Info

Publication number: DD234574A3
Authority: DD; German Democratic Republic
Prior art keywords: pyrid; mol; dimethylformamide; dihydro; formula
Prior art date: 1982-05-28

Application number

DD24030482A

Other languages

German (de)

English (en)

Inventor

Eberhard Schroetter

Hans Ulrich Heyne

Hartmut Niedrich

Hans Schick

Hellmut Landmann

Johannes Oehlke

Dieter Lohmann

Gottfried Faust

Hans-Joachim Heidrich

Hans-Joachim Jaensch

Original Assignee

Akad Wissenschaften Ddr

Niedrich

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.)

1982-05-28

Filing date

1982-05-28

Publication date

1986-04-09

1982-05-28 Application filed by Akad Wissenschaften Ddr, Niedrich filed Critical Akad Wissenschaften Ddr

1982-05-28 Priority to DD24030482A priority Critical patent/DD234574A3/de

1983-05-12 Priority to YU105483A priority patent/YU105483A/xx

1983-05-19 Priority to CS833549A priority patent/CS354983A1/cs

1983-05-27 Priority to HU189583A priority patent/HU191847B/hu

1986-04-09 Publication of DD234574A3 publication Critical patent/DD234574A3/de

Links

238000004519 manufacturing process Methods 0.000 title abstract description 3
RNLQIBCLLYYYFJ-UHFFFAOYSA-N amrinone Chemical compound N1C(=O)C(N)=CC(C=2C=CN=CC=2)=C1 RNLQIBCLLYYYFJ-UHFFFAOYSA-N 0.000 title abstract 2
238000000034 method Methods 0.000 claims abstract description 35
150000001875 compounds Chemical class 0.000 claims abstract description 5
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 153
238000006243 chemical reaction Methods 0.000 claims description 19
DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 13
150000001412 amines Chemical class 0.000 claims description 12
150000003222 pyridines Chemical class 0.000 claims description 11
150000004820 halides Chemical class 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
230000015556 catabolic process Effects 0.000 claims description 3
238000006731 degradation reaction Methods 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
SJSWRKNSCWKNIR-UHFFFAOYSA-N azane;dihydrochloride Chemical compound N.Cl.Cl SJSWRKNSCWKNIR-UHFFFAOYSA-N 0.000 claims description 2
150000003857 carboxamides Chemical class 0.000 claims description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
230000007062 hydrolysis Effects 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
150000002826 nitrites Chemical class 0.000 claims 1
150000003839 salts Chemical class 0.000 abstract description 23
239000002351 wastewater Substances 0.000 abstract description 5
230000003177 cardiotonic effect Effects 0.000 abstract description 3
239000002994 raw material Substances 0.000 abstract description 3
230000002804 anti-anaphylactic effect Effects 0.000 abstract description 2
230000002349 favourable effect Effects 0.000 abstract description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 69
FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 46
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
239000000243 solution Substances 0.000 description 35
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 27
235000011121 sodium hydroxide Nutrition 0.000 description 23
239000000203 mixture Substances 0.000 description 21
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
-1 halide phosphorus oxychloride Chemical class 0.000 description 14
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 12
150000001408 amides Chemical class 0.000 description 12
150000002825 nitriles Chemical class 0.000 description 12
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
238000001816 cooling Methods 0.000 description 11
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl chloride Substances ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 11
239000002904 solvent Substances 0.000 description 11
239000000047 product Substances 0.000 description 10
238000003756 stirring Methods 0.000 description 10
239000002585 base Substances 0.000 description 9
239000012452 mother liquor Substances 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
238000010438 heat treatment Methods 0.000 description 7
ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
229910052783 alkali metal Inorganic materials 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
239000013078 crystal Substances 0.000 description 6
JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Chemical compound Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 description 6
WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 6
238000002955 isolation Methods 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
229910000029 sodium carbonate Inorganic materials 0.000 description 6
159000000000 sodium salts Chemical class 0.000 description 6
PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical class NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 5
239000005708 Sodium hypochlorite Substances 0.000 description 5
239000003513 alkali Substances 0.000 description 5
150000008044 alkali metal hydroxides Chemical class 0.000 description 5
238000001035 drying Methods 0.000 description 5
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 5
238000010626 work up procedure Methods 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
229910000288 alkali metal carbonate Inorganic materials 0.000 description 4
150000008041 alkali metal carbonates Chemical class 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
238000007363 ring formation reaction Methods 0.000 description 4
239000000725 suspension Substances 0.000 description 4
238000005406 washing Methods 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
235000011181 potassium carbonates Nutrition 0.000 description 3
239000007787 solid Substances 0.000 description 3
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
238000003915 air pollution Methods 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
238000004140 cleaning Methods 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000012458 free base Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
125000000896 monocarboxylic acid group Chemical group 0.000 description 2
OWVFJYJLBSWYII-UHFFFAOYSA-N n,n-dimethyl-2-pyridin-4-ylethenamine Chemical compound CN(C)C=CC1=CC=NC=C1 OWVFJYJLBSWYII-UHFFFAOYSA-N 0.000 description 2
229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
235000015497 potassium bicarbonate Nutrition 0.000 description 2
239000011736 potassium bicarbonate Substances 0.000 description 2
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000006798 ring closing metathesis reaction Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
BSADJIPSKPADNV-UHFFFAOYSA-N 4-methylpyridin-1-ium;chloride Chemical compound Cl.CC1=CC=NC=C1 BSADJIPSKPADNV-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-M L-tartrate(1-) Chemical compound OC(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-M 0.000 description 1
QXHXMALPRIXDEU-UHFFFAOYSA-P [3-(dimethylamino)-2-[(dimethylazaniumyl)methyl]prop-2-enyl]-dimethylazanium Chemical class CN(C)C=C(C[NH+](C)C)C[NH+](C)C QXHXMALPRIXDEU-UHFFFAOYSA-P 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
229940072107 ascorbate Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
239000012267 brine Substances 0.000 description 1
230000007883 bronchodilation Effects 0.000 description 1
229940124630 bronchodilator Drugs 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
238000005266 casting Methods 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
NSNHWTBQMQIDCF-UHFFFAOYSA-N dihydrate;hydrochloride Chemical compound O.O.Cl NSNHWTBQMQIDCF-UHFFFAOYSA-N 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-M fumarate(1-) Chemical compound OC(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-M 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000009413 insulation Methods 0.000 description 1
238000011068 loading method Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000000870 ultraviolet spectroscopy Methods 0.000 description 1

Landscapes

Pyridine Compounds (AREA)

DD24030482A 1982-05-28 1982-05-28 Verfahren zur herstellung von 3-amino-5-(pyrid-4-yl)-1,2-dihydro-pyrid-2-on DD234574A3 (de)

Priority Applications (4)

Application Number	Priority Date	Filing Date	Title
DD24030482A DD234574A3 (de)	1982-05-28	1982-05-28	Verfahren zur herstellung von 3-amino-5-(pyrid-4-yl)-1,2-dihydro-pyrid-2-on
YU105483A YU105483A (en)	1982-05-28	1983-05-12	Process for obtaining 3-amino-5-(pyrid-4'yl)-1,2-dihydro-pyrid-2-one
CS833549A CS354983A1 (en)	1982-05-28	1983-05-19	Zpusob vyroby 3.amino050 lpyridin 4 yl p 1,2 dihydropyrid 2 onu
HU189583A HU191847B (en)	1982-05-28	1983-05-27	Process for producing 3-amino-5-/pyridin-4-yl/-1,2-dihydro-pyridin-2-one compound

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DD24030482A DD234574A3 (de)	1982-05-28	1982-05-28	Verfahren zur herstellung von 3-amino-5-(pyrid-4-yl)-1,2-dihydro-pyrid-2-on

Publications (1)

Publication Number	Publication Date
DD234574A3 true DD234574A3 (de)	1986-04-09

Family

ID=5538925

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD24030482A DD234574A3 (de)	1982-05-28	1982-05-28	Verfahren zur herstellung von 3-amino-5-(pyrid-4-yl)-1,2-dihydro-pyrid-2-on

Country Status (4)

Country	Link
CS (1)	CS354983A1 (cs)
DD (1)	DD234574A3 (cs)
HU (1)	HU191847B (cs)
YU (1)	YU105483A (cs)

1982
- 1982-05-28 DD DD24030482A patent/DD234574A3/de unknown
1983
- 1983-05-12 YU YU105483A patent/YU105483A/xx unknown
- 1983-05-19 CS CS833549A patent/CS354983A1/cs unknown
- 1983-05-27 HU HU189583A patent/HU191847B/hu unknown

Also Published As

Publication number	Publication date
HU191847B (en)	1987-04-28
CS354983A1 (en)	1985-07-16
YU105483A (en)	1986-02-28

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