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

HRID 1413935Notes

Reaction equation

HRID 1413935 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-ae78666f76aa4455879a55205c37c960
Source dataset
uspto-grants-1981_02
Patent number
US04251661

Reaction notes

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