Leflunomide → 4-(Trifluoromethyl)aniline

HRID 2086371Notes

Reaction equation

HRID 2086371 reaction equation
CC1ON=CC=1C([NH:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:14][CH:15]=1)=O.[CH3:20][C:21]1[O:25][N:24]=[CH:23][C:22]=1[C:26]([OH:28])=[O:27]>>[F:17][C:16]([F:18])([F:19])[C:13]1[CH:14]=[CH:15][C:10]([NH2:9])=[CH:11][CH:12]=1.[CH3:20][C:21]1[O:25][N:24]=[CH:23][C:22]=1[C:26]([OH:28])=[O:27]

Participants

4

Reactant 2

HCID 3899LeflunomideHCID 14252405-Methylisoxazole-4-carboxylic acid

Product 2

HCID 99644-(Trifluoromethyl)anilineHCID 14252405-Methylisoxazole-4-carboxylic acid

Procedure

A process for synthesizing leflunomide from 5-methylisoxazole-4-carboxylic acid and 4-trifluoromethylaniline is provided in which the carboxylic acid group of 5-methylisoxazole-4-carboxylic acid is chlorinated, forming 5-methylisoxazole-4-carboxylic acid chloride. The acid chloride is then reacted without intermediate distillation with 4-trifluoromethylaniline in the presence of an alkali metal or alkaline-earth metal bicarbonate acid scavenger.

Sources & evidence

ORD record
ord-6934a2ba5240440b84303e5c9cde0c8c
Source dataset
uspto-grants-2004_04
Patent number
US06723855B2

Reaction notes

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