LU82648A1 - Procede de preparation de 1,2-dihydro-2-oxo-5-(pyridinyl)nicotinonitriles - Google Patents

Procede de preparation de 1,2-dihydro-2-oxo-5-(pyridinyl)nicotinonitriles Download PDF

Info

Publication number: LU82648A1
Authority: LU; Luxembourg
Prior art keywords: pyridinyl; dihydro; oxo; acrolein; ethanol
Prior art date: 1979-07-26

Application number

LU82648A

Other languages

English (en)

French (fr)

Original Assignee

Sterling Drug Inc

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.)

1979-07-26

Filing date

1980-07-21

Publication date

1981-02-02

1980-07-21 Application filed by Sterling Drug Inc filed Critical Sterling Drug Inc

1981-02-02 Publication of LU82648A1 publication Critical patent/LU82648A1/fr

Links

238000000034 method Methods 0.000 title claims description 24
238000002360 preparation method Methods 0.000 title claims description 8
FIULGFJIHJJXMT-UHFFFAOYSA-N [C]1[N]C=CC=C1 Chemical class [C]1[N]C=CC=C1 FIULGFJIHJJXMT-UHFFFAOYSA-N 0.000 title 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 30
-1 4-pyridinyl Chemical group 0.000 claims description 24
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 24
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 15
JXPDNDHCMMOJPC-UHFFFAOYSA-N 2-hydroxybutanedinitrile Chemical compound N#CC(O)CC#N JXPDNDHCMMOJPC-UHFFFAOYSA-N 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 7
238000006243 chemical reaction Methods 0.000 claims description 7
238000010992 reflux Methods 0.000 claims description 6
SEQOYYYZFNJQSV-UHFFFAOYSA-N 2-oxo-5-pyridin-4-yl-1h-pyridine-3-carbonitrile Chemical compound C1=C(C#N)C(=O)NC=C1C1=CC=NC=C1 SEQOYYYZFNJQSV-UHFFFAOYSA-N 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
NTHQYHTZRJMPFI-UHFFFAOYSA-N 2-oxo-5-pyridin-2-yl-1h-pyridine-3-carbonitrile Chemical compound C1=C(C#N)C(=O)NC=C1C1=CC=CC=N1 NTHQYHTZRJMPFI-UHFFFAOYSA-N 0.000 claims description 3
238000010438 heat treatment Methods 0.000 claims description 3
150000002500 ions Chemical class 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
239000000203 mixture Substances 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
PNAHPHGJXNKLNF-UHFFFAOYSA-N 3-(dimethylamino)-2-pyridin-4-ylprop-2-enal Chemical compound CN(C)C=C(C=O)C1=CC=NC=C1 PNAHPHGJXNKLNF-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
235000005152 nicotinamide Nutrition 0.000 description 2
150000005480 nicotinamides Chemical class 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000007787 solid Substances 0.000 description 2
UAOTWASOGSHQAI-UHFFFAOYSA-N 2-methoxy-5-pyridin-4-ylpyridine-3-carbonitrile Chemical compound C1=C(C#N)C(OC)=NC=C1C1=CC=NC=C1 UAOTWASOGSHQAI-UHFFFAOYSA-N 0.000 description 1
KFPKURCPGZGYHR-UHFFFAOYSA-N 2-oxo-5-pyridin-3-yl-1h-pyridine-3-carbonitrile Chemical compound C1=C(C#N)C(=O)NC=C1C1=CC=CN=C1 KFPKURCPGZGYHR-UHFFFAOYSA-N 0.000 description 1
ZQMMLUFYTCOQTB-UHFFFAOYSA-N 2-pyridin-2-ylpropanedial Chemical compound O=CC(C=O)C1=CC=CC=N1 ZQMMLUFYTCOQTB-UHFFFAOYSA-N 0.000 description 1
OTIZLYDEBSAMGZ-UHFFFAOYSA-N 3-amino-5-pyridin-2-yl-1h-pyridin-2-one Chemical class N1C(=O)C(N)=CC(C=2N=CC=CC=2)=C1 OTIZLYDEBSAMGZ-UHFFFAOYSA-N 0.000 description 1
GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 1
XPKCTVWRMHSHFC-UHFFFAOYSA-N 5-(2-methylpyridin-3-yl)-2-oxo-1h-pyridine-3-carbonitrile Chemical compound CC1=NC=CC=C1C1=CNC(=O)C(C#N)=C1 XPKCTVWRMHSHFC-UHFFFAOYSA-N 0.000 description 1
PNWCHLYSZPVAPM-UHFFFAOYSA-N 5-(3-ethylpyridin-4-yl)-2-oxo-1h-pyridine-3-carbonitrile Chemical compound CCC1=CN=CC=C1C1=CNC(=O)C(C#N)=C1 PNWCHLYSZPVAPM-UHFFFAOYSA-N 0.000 description 1
SCMAWGKXZZAPPO-UHFFFAOYSA-N 5-(4,6-dimethylpyridin-2-yl)-2-oxo-1h-pyridine-3-carbonitrile Chemical compound CC1=CC(C)=NC(C=2C=C(C(=O)NC=2)C#N)=C1 SCMAWGKXZZAPPO-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 description 1
KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
239000000496 cardiotonic agent Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
230000037230 mobility Effects 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
230000009466 transformation Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pyridine Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

LU82648A 1979-07-26 1980-07-21 Procede de preparation de 1,2-dihydro-2-oxo-5-(pyridinyl)nicotinonitriles LU82648A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/060,758 US4223149A (en)	1979-07-26	1979-07-26	Process for producing 3-cyano-5-(pyridinyl)-2(1H)-pyridinones
US6075879		1979-07-26

Publications (1)

Publication Number	Publication Date
LU82648A1 true LU82648A1 (fr)	1981-02-02

Family

ID=22031563

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU82648A LU82648A1 (fr)	1979-07-26	1980-07-21	Procede de preparation de 1,2-dihydro-2-oxo-5-(pyridinyl)nicotinonitriles

Country Status (15)

Country	Link
US (1)	US4223149A (de)
JP (1)	JPS5620573A (de)
AR (1)	AR226853A1 (de)
AT (1)	ATA363280A (de)
CA (1)	CA1132570A (de)
DK (1)	DK313580A (de)
ES (1)	ES493497A0 (de)
FI (1)	FI802283A7 (de)
GR (1)	GR69739B (de)
LU (1)	LU82648A1 (de)
NL (1)	NL8004103A (de)
NO (1)	NO802137L (de)
PT (1)	PT71539A (de)
SE (1)	SE8005287L (de)
ZA (1)	ZA804171B (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4365065A (en) *	1979-11-26	1982-12-21	Sterling Drug Inc.	1-(Pyridinyl)-2-(dimethylamino)ethenyl lower-alkyl ketones
US4347363A (en) *	1981-09-17	1982-08-31	Sterling Drug Inc.	Process for preparing 1,2-dihydro-6-methyl-2-oxo-5-(pyridinyl)nicotinonitriles
US4432979A (en) *	1981-10-26	1984-02-21	William H. Rorer, Inc.	Pyridone compounds
US4469871A (en) *	1982-05-24	1984-09-04	Sterling Drug Inc.	Process for preparing 2-(lower-alkoxy)-1-(pyridinyl) ethenyl lower-alkyl ketones
US4417054A (en) *	1982-05-24	1983-11-22	Sterling Drug Inc.	2-(Lower-alkoxy)-1-(pyridinyl)ethenyl lower-alkyl ketones
NO163008C (no) *	1982-05-24	1990-03-21	Sterling Drug Inc	2-(laverealkoksy)-1-(pyridinyl)etenyl-lavere-alkylketon og fremgangsmaate for fremstilling av pyridinylnikotinderivater.
US4413127A (en) *	1982-05-24	1983-11-01	Sterling Drug Inc.	Preparation of 1,2-dihydro-6-(lower alkyl)-2-oxo-5-(pyridinyl)nicotinonitriles

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4072746A (en) *	1975-10-14	1978-02-07	Sterling Drug Inc.	3-Amino-5-(pyridinyl)-2(1H)-pyridinones
US4004012A (en) *	1975-10-14	1977-01-18	Sterling Drug Inc.	3-Cyano-5-(pyridinyl)-2(1H)-pyridinones

1979
- 1979-07-26 US US06/060,758 patent/US4223149A/en not_active Expired - Lifetime
1980
- 1980-01-28 GR GR62455A patent/GR69739B/el unknown
- 1980-07-02 AR AR281620A patent/AR226853A1/es active
- 1980-07-11 ZA ZA00804171A patent/ZA804171B/xx unknown
- 1980-07-11 AT AT0363280A patent/ATA363280A/de not_active IP Right Cessation
- 1980-07-11 PT PT71539A patent/PT71539A/pt unknown
- 1980-07-16 NO NO802137A patent/NO802137L/no unknown
- 1980-07-16 NL NL8004103A patent/NL8004103A/nl not_active Application Discontinuation
- 1980-07-18 ES ES493497A patent/ES493497A0/es active Granted
- 1980-07-18 FI FI802283A patent/FI802283A7/fi not_active Application Discontinuation
- 1980-07-21 JP JP9974080A patent/JPS5620573A/ja active Pending
- 1980-07-21 SE SE8005287A patent/SE8005287L/xx unknown
- 1980-07-21 LU LU82648A patent/LU82648A1/fr unknown
- 1980-07-21 DK DK313580A patent/DK313580A/da not_active Application Discontinuation
- 1980-07-23 CA CA356,861A patent/CA1132570A/en not_active Expired

Also Published As

Publication number	Publication date
NL8004103A (nl)	1981-01-28
ES8105995A1 (es)	1981-07-01
FI802283A7 (fi)	1981-01-01
ES493497A0 (es)	1981-07-01
AR226853A1 (es)	1982-08-31
ATA363280A (de)	1984-02-15
ZA804171B (en)	1981-07-29
US4223149A (en)	1980-09-16
PT71539A (en)	1980-08-01
CA1132570A (en)	1982-09-28
NO802137L (no)	1981-01-27
JPS5620573A (en)	1981-02-26
DK313580A (da)	1981-01-27
GR69739B (de)	1982-07-09
SE8005287L (sv)	1981-01-27

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