Hydrochloric Acid → 2-(3-Bromophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(3-bromo-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (7 g, 18 mmol) in methanol (25 mL) and tetrahydrofuran (100 mL), 30% sodium hydroxide in water (20 mL) was stirred at 60° C. for 56 h. The mixture was neutralized with a 3 N aqueous hydrochloric acid solution and extracted with ethyl acetate (2×100 mL), washed with water, dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 2-(3-bromo-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (6.4 g, 88%) as a brown solid which was used for next step without further purification: LC/MS m/e calcd for C18H18BrNO2 (M+H)+: 361.25, observed: 360.2.

Provenance & Evidence