Title:
METHOD FOR PRODUCING 5-FLUORO-1H-PYRAZOLE-4-CARBOXYLIC ACIDS
Document Type and Number:
Japanese Patent JP2013023476
Kind Code:
A
Abstract:
To provide a simple and highly-efficient method for producing 5-fluoro-1H-pyrazole-4-carboxylic acids which are useful as a medical/agricultural agent or a synthetic intermediate thereof.
In this method, 5-fluoro-1H-pyrazole-4-carboxylic acids represented by general formula (3) (in the formula, R1 represents a 1-6C alkyl group or the like. R2 represents a 1-4C alkyl group or the like. R3 represents a phenyl group or the like. X represents an oxygen atom, an imino group or the like.) are produced by reacting α-trifluoromethyl-β-keto-carboxylic acid with hydrazines, according to circumstances, in the presence of a base.
Inventors:
YAMAKAWA SATORU
OTSUKA TAKENORI
OTSUKA TAKENORI
Application Number:
JP2011160470A
Publication Date:
February 04, 2013
Filing Date:
July 22, 2011
Export Citation:
Assignee:
SAGAMI CHEMICAL RES INST
TOSOH F TECH INC
TOSOH F TECH INC
International Classes:
C07D231/16; C07C249/16; C07C251/76
Domestic Patent References:
| JP2002524449A | 2002-08-06 | |||
| JP2005501044A | 2005-01-13 | |||
| JP2005523934A | 2005-08-11 | |||
| JP2009535379A | 2009-10-01 | |||
| JP2008280250A | 2008-11-20 | |||
| JP2009530343A | 2009-08-27 | |||
| JPH05230029A | 1993-09-07 |
Other References:
VOLLE,J. ET AL: "Fluorine-sacrificial cyclizations as an access to 5-fluoropyrazoles", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, JPN6015016112, 2000, pages 823 - 828, ISSN: 0003059227
FURIN,G.G. ET AL: "Reactions of perfluoro(5-aza-4-nonene) with hydrazine and some its derivatives", RUSSIAN JOURNAL OF ORGANIC CHEMISTRY(TRANSLATION OF ZHURNAL ORGANICHESKOI KHIMII), vol. 37, no. 11, JPN6015016114, 2001, pages 1621 - 1628, XP002734818, ISSN: 0003059228, DOI: 10.1023/A:1013876707892
CHI,K. ET AL: "Synthesis of fluorinated N-arylpyrazoles with perfluoro-2-methyl-2-pentene and arylhydrazines", JOURNAL OF FLUORINE CHEMISTRY, vol. 98, no. 1, JPN6015016118, 1999, pages 29 - 36, XP002727520, ISSN: 0003059229, DOI: 10.1016/S0022-1139(99)00079-2
KATRITZKY,A.R. ET AL: "Mechanisms of heterocycle ring formation. Part 5. A carbon-13 nuclear magnetic resonance study of py", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 2: PHYSICAL ORGANIC CHEMISTRY, JPN6015016119, 1987, pages 969 - 975, XP002100028, ISSN: 0003059230, DOI: 10.1039/p29870000969
BUKAC,Z. ET AL: "Alkaline polymerization of 6-caprolactam. XXX. Formation of uracils and 2(1H)-pyridones during therm", COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, vol. 32, no. 10, JPN6015016120, 1967, pages 3537 - 3545, ISSN: 0003059231
SEARLES,A.L. ET AL: "Alkylation and cyclization of benzoylacetanilides", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 80, JPN6015016116, 1958, pages 3656 - 3663, ISSN: 0003059232
FURIN,G.G. ET AL: "Reactions of perfluoro(5-aza-4-nonene) with hydrazine and some its derivatives", RUSSIAN JOURNAL OF ORGANIC CHEMISTRY(TRANSLATION OF ZHURNAL ORGANICHESKOI KHIMII), vol. 37, no. 11, JPN6015016114, 2001, pages 1621 - 1628, XP002734818, ISSN: 0003059228, DOI: 10.1023/A:1013876707892
CHI,K. ET AL: "Synthesis of fluorinated N-arylpyrazoles with perfluoro-2-methyl-2-pentene and arylhydrazines", JOURNAL OF FLUORINE CHEMISTRY, vol. 98, no. 1, JPN6015016118, 1999, pages 29 - 36, XP002727520, ISSN: 0003059229, DOI: 10.1016/S0022-1139(99)00079-2
KATRITZKY,A.R. ET AL: "Mechanisms of heterocycle ring formation. Part 5. A carbon-13 nuclear magnetic resonance study of py", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 2: PHYSICAL ORGANIC CHEMISTRY, JPN6015016119, 1987, pages 969 - 975, XP002100028, ISSN: 0003059230, DOI: 10.1039/p29870000969
BUKAC,Z. ET AL: "Alkaline polymerization of 6-caprolactam. XXX. Formation of uracils and 2(1H)-pyridones during therm", COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, vol. 32, no. 10, JPN6015016120, 1967, pages 3537 - 3545, ISSN: 0003059231
SEARLES,A.L. ET AL: "Alkylation and cyclization of benzoylacetanilides", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 80, JPN6015016116, 1958, pages 3656 - 3663, ISSN: 0003059232
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