IP Library Granted Patent US 7,488,828
Granted Patent B2
US 7,488,828 · App. 11/166,485 · Granted Feb 10, 2009

Process for the preparation of 4-trifluoromethyl-2(1H)-pyridinone

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Quick Facts
Patent No.
US 7,488,828
App. No.
11/166,485
Granted
Feb 10, 2009
Kind
B2
Abstract

4-Trifluoromethyl-2(1H)-pyridinone is prepared by reaction of 4-alkoxy-1,1,1-trifluorobut-3-en-2-one or 4,4-dialkoxy-1,1,1-trifluorobutan-2-one with a trialkyl phosphonoacetate followed by cyclization.

Claims (14)

1. A process for the preparation of 4-trifluoromethyl-2(1H)-pyridinone (I),

which comprises:

i) contacting either a 4-alkoxy-1,1,1-trifluorobut-3-en-2-one of the formula

in which R represents C 1 -C 4 alkyl, or a 4,4-dialkoxy-1,1,1-trifluorobutan-2-one of the formula

in which R is as previously defined, with a trialkyl phosphonoacetate of the formula:

in which R is as previously defined, in the presence of a base and an alcohol or glycol solvent to provide a mixture of condensation products of the formula

in which R is as previously defined;

and

ii) cyclizing the mixture of condensation products to provide 4-trifluoromethyl-2(1H)-pyridinone.

2. The process of claim 1 in which the mixture of condensation products is cyclized by reacting with an ammonium salt of an organic acid and/or with a mineral acid and/or with formamide.

3. The process of claim 2 in which the ammonium salt of an organic acid is ammonium formate or ammonium acetate.

4. The process of claim 1 in which the mixture of condensation products is cyclized by reacting with an unsubstituted amide and methoxide to form a mixture of amides which is subsequently cyclized with acid.

5. The process of claim 1 in which the mixture of condensation products is cyclized by reacting with an acid and water to form the lactone which is subsequently reacted with ammonia.

6. The process of claim 1 in which the mixture of condensation products is cyclized by reacting with an organic anhydride and pyridinium p-toluenesulfonate (PPTS) to form a mixture of dieneoates which is subsequently cyclized by reacting with an ammonium salt of an organic acid (R′ represents alkyl or aryl) or a mineral acid or with formamide or by reacting with an unsubstituted amide and methoxide to form a mixture of amides which is subsequently cyclized with acid.

Assignments (2)
CHANGE OF NAME Recorded Nov 8, 2021
From: DOW AGROSCIENCES LLC
To: CORTEVA AGRISCIENCE LLC
Reel/Frame 058044/0184 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 12, 2008
From: HAMILTON, CHRISTOPHER T.; GULLO, MICHAEL F.; GONZALEZ, MICHAEL A.; ROTH, GARY A.; GORMAN, DAVID B.; GEBHARDT, JOACHIM; MAYER, GUIDO; RACK, MICHAEL; JAEDICKE, HAGEN; GOTZ, NORBERT
To: DOW AGROSCIENCES LLC
Reel/Frame 021374/0041 →