Acetone → 2-(trifluoromethyl)quinoline-4-carboxylic acid

HRID 2286702Notes

Reaction equation

HRID 2286702 reaction equation
CC1C=[C:10]([C:12]([OH:14])=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.N1C2C(=CC=CC=2)C(=O)C1=O.CC(C)=O.[F:30][C:31]([F:36])([F:35])[C:32]([CH3:34])=O>[OH-].[K+]>[F:30][C:31]([F:36])([F:35])[C:32]1[CH:34]=[C:10]([C:12]([OH:14])=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 7054Isatin2×HCID 9871Methyl trifluoromethyl ketoneHCID 6044422-methylquinoline-4-carboxylic acid

Product 1

HCID 95477122-(trifluoromethyl)quinoline-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

2-Methylcinchoninic acid has been prepared, as disclosed in Bull. Soc. Chem., France, 1956, 1294, by the reaction of isatin and acetone in 30 percent aqueous potassium hydroxide solution. However, it has been found that when isatin is reacted with 1,1,1-trifluoroacetone in an attempt to produce 2-trifluoromethyl cinchoninic acid in an analogous manner, the desired product cannot be obtained.

Sources & evidence

ORD record
ord-8ef972ca10ed432091e55ba22f676b1a
Source dataset
uspto-grants-1981_05
Patent number
US04267333

Reaction notes

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