Methanol → HCID 68505396, compound

Participants

Reaction Conditions

Reaction Steps

Thionyl chloride (13 g; 1.5 equiv.) was added dropwise at 0° C., in the course of 5-10 minutes, to a solution of crude 2-(1,2,3,4-tetrahydroquinolin-7-yl)acetic acid (stage 5; 14 g; 1 equiv.) in 140 ml of methanol, and the resulting reaction mixture was then heated for 6 hours at reflux (70° C.). When the conversion was complete, the reaction solution was concentrated under reduced pressure and the residue was taken up in 150 ml of water, rendered basic (pH 7-8) with sodium carbonate and finally extracted with 2×150 ml of chloroform. The combined organic phases were dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 10-12% ethyl acetate/-hexane). Methyl 2-(1,2,3,4-tetrahydroquinolin-7-yl)acetate (4 g) was obtained in the form of a colorless oil.

Provenance & Evidence