EP 1529029 A1 20050511 - METHOD FOR PRODUCING 3-AMINO-4,4,4-TRIFLUOROCROTONIC ACID ESTERS
Title (en)
METHOD FOR PRODUCING 3-AMINO-4,4,4-TRIFLUOROCROTONIC ACID ESTERS
Title (de)
VERFAHREN ZUR HERSTELLUNG VON 3-AMINO-4,4,4-TRIFLUORCROTONSÄUREESTERN
Title (fr)
PROCEDE DE PRODUCTION D'ESTERS D'ACIDE 3,AMINO-4,4,4-TRIFLUOROCROTONIQUE
Publication
Application
Priority
- DE 10237285 A 20020814
- EP 0309006 W 20030813
Abstract (en)
[origin: WO2004016579A1] The invention relates to a method for producing 3-amino-4,4,4-trifluorocrotonic acid esters of formula (I) or their E/Z isomers or tautomeric forms, whereby R<1> and R<2>, independent of one another, represent hydrogen, an optionally substituted linear C1-C4 alkyl radical or an optionally substituted benzyl radical, and R<3> represents methyl or ethyl. The inventive method is characterized in that: a) an alkyl trifluoroacetate is reacted with an alkyl acetate of formula CH3-CO-OR<3> and with an alkali metal alcoholate to form an enolate of a trifluoroacetoacetic acid ester of formula (II), whereby M represents sodium or potassium, and R<3> has the aforementioned meaning, and afterwards; b) the alkali enolate of the trifluoroacetoacetic acid ester from step a) can, without further purification, directly react with an amine of formula NHR<1>R<2> in the presence of an acid to form 3-amino-4,4,4-trifluorocrotonic acid esters. This two-step method enables the production of 3-amino-4,4,4- trifluorocrotonic acid esters in high yields without resulting in the formation of significant byproducts.
IPC 1-7
IPC 8 full level
C07C 213/02 (2006.01); C07C 219/20 (2006.01); C07C 227/08 (2006.01); C07C 229/30 (2006.01)
CPC (source: EP US)
C07C 227/08 (2013.01 - EP US)
C-Set (source: EP US)
Designated contracting state (EPC)
AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LI LU MC NL PT RO SE SI SK TR
DOCDB simple family (publication)
WO 2004016579 A1 20040226; AU 2003263217 A1 20040303; DE 10237285 A1 20040226; EP 1529029 A1 20050511; JP 2005535713 A 20051124; US 2005182272 A1 20050818; US 7002038 B2 20060221
DOCDB simple family (application)
EP 0309006 W 20030813; AU 2003263217 A 20030813; DE 10237285 A 20020814; EP 03787790 A 20030813; JP 2004528491 A 20030813; US 51193204 A 20041018