P-Anisidine → HCID 178487932, compound

HRID 1196569Notes

Reaction equation

HRID 1196569 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3](=O)[CH2:4][C:5]([O:7]CC)=O.[CH3:13][O:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1>>[F:12][C:2]([F:1])([F:11])[C:3]1[CH:4]=[C:5]([OH:7])[C:20]2[C:18](=[CH:17][CH:16]=[C:15]([O:14][CH3:13])[CH:21]=2)[N:19]=1

Participants

3

Reactant 2

HCID 7732P-AnisidineHCID 67793Ethyl 4,4,4-trifluoroacetoacetate

Product 1

HCID 178487932HCID 178487932, compound

Procedure

Ethyl trifluoroacetoacetate and 4-methoxyaniline were reacted together in presence of polyphosphoric acid to give 2-trifluoromethyl-4-hydroxy-6-methoxyquinoline (cf. Jouillie and Dey). The latter was converted to 2-trifluoromethyl-4-chloro-6-methoxy-quinoline by analogy with Example IV. This was in turn converted first to 2-trifluoromethyl-6-methoxyquinoline by hydrogenation in the presence of palladium on charcoal and thence to 2-trifluoromethyl-6-hydroxyquinoline by reaction with aqueous hydrobromic acid. The latter was reacted with (8-bromo-1-tetrahydro pyranyloxy)octane according to Example BIII, 8(2-trifluoromethyl-6-quinolinyloxy)octane-1-ol was prepared and used in Stage b.

Sources & evidence

ORD record
ord-a94c981714da4126bd60598b4b1a1b52
Source dataset
uspto-grants-1992_05
Patent number
US05114940

Reaction notes

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