Hexane → HCID 178477332, compound

Participants

Reaction Conditions

Reaction Steps

5.8 ml (11.6 mmol, 2M in toluene)trimethyl aluminium and 1.5 g (11.6 mmol) 3-fluorobenzylamine were added in succession to a solution of 1.0 g (2.9 mmol) 2-(ethylthio)-4-hydroxy-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester in toluene (18 ml) and the mixture was then heated for 2 h at 80° C. Then it was diluted with water and extracted with EE. The organic phase was washed with 1M hydrochloric acid, water and brine, dried over Na2SO4, filtered and concentrated to small volume under vacuum. Column chromatography (hexane/EE 17:3) of the residue yielded 0.9 g (2.1 mmol, 73%) 2-(ethylthio)-N-(3-fluorobenzyl)-4-hydroxy-7-(trifluoromethyl)quinoline-3-carboxamide.

Provenance & Evidence