Aniline → HCID 178516132, compound

HRID 1196566Notes

Reaction equation

HRID 1196566 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3](=O)[CH2:4][C:5]([O:7]CC)=O.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[F:12][C:2]([F:1])([F:11])[C:3]1[CH:4]=[C:5]([OH:7])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1

Participants

3

Reactant 2

HCID 6115AnilineHCID 67793Ethyl 4,4,4-trifluoroacetoacetate

Product 1

HCID 178516132HCID 178516132, compound

Procedure

Ethyl trifluoroacetoacetate (3.7 g) and aniline (1.8 ml) were reacted together in polyphosphoric acid according to Joullie et al, J. Med. Chem., 16, 134 (1973), to give 2-trifluoromethyl-4-hydroxyquinoline (1.8 g). The latter was reacted with phosphorous oxychloride and phosphorous pentachloride in a similar fashion to Example VIII to give 2-trifluoromethyl-4-chloroquinoline, which was used in Stage a.

Sources & evidence

ORD record
ord-07d8f48a4c8e4a7bbe58c5f334519f30
Source dataset
uspto-grants-1992_05
Patent number
US05114940

Reaction notes

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