Sodium Hydroxide → (E)-4-methyl-2-(prop-1-enyl)-7-(trifluoromethyl)quinoline-3-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

560 mg (13.9 mmol) NaOH flocs were added to a solution of 450 mg (1.4 mmol) (E)-4-methyl-2-(prop-1-enyl)-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester in a water/EtOH mixture (in each case 21 ml) at 0° C. The mixture was subsequently heated to 90° C. for 16 h. It was then concentrated in a vacuum and the residue was taken up with water (20 ml) and washed with EtOAc. Thereafter, the aqueous phase was set to pH ˜2 with a 2M hydrochloric acid and extracted with EtOAc. The organic phase was dried over Na2SO4 and concentrated in a vacuum. 350 mg (1.2 mmol, 85%) (E)-4-methyl-2-(prop-1-enyl)-7-(trifluoromethyl)quinoline-3-carboxylic acid was obtained as a residue. The raw product was further converted without additional purification.

Provenance & Evidence