Aniline → HCID 178516126, compound

HRID 1196548Notes

Reaction equation

HRID 1196548 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:8][C:9]([F:19])([F:18])[C:10](=O)[CH2:11][C:12](OCC)=[O:13]>>[OH:13][C:12]1[CH:11]=[C:10]([C:9]([F:19])([F:18])[F:8])[C:7]2[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:1]=1

Participants

3

Reactant 2

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

Product 1

HCID 178516126HCID 178516126, compound

Procedure

Aniline (ex Aldrich) and ethyl trifluoroacetoacetate (ex Lancaster) were reacted together according to Westland et al, J. Med. Chem., 16, 326 (1973), to give 2-hydroxy-4-trifluoromethylquinoline. The latter (2.5 g), was treated for 30 minutes at 90°-100° C. with phosphorous oxychloride (20 ml) and resublimed phosphorous pentachloride (2.45 g). The reaction mixture was allowed to cool and poured onto ice-water and neutralised with aqueous ammonium hydroxide. Extraction into diethyl ether yielded 2-chloro-4-trifluoromethyl quinoline, which after conventional work-up was used directly in Stage a.

Sources & evidence

ORD record
ord-bc1977101ad140bdb91210c5b5acb188
Source dataset
uspto-grants-1992_05
Patent number
US05114940

Reaction notes

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