Acetyl chloride → HCID 20450114, compound

Participants

Reaction Steps

Methyl 2-amino-6-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylate hydrochloride (13.6 g., 50 mM) was suspended in dry dichloromethane (200 ml.). The suspension was stirred and cooled in ice, and dry triethylamine (16.8 ml., 120 mM) was added, followed by acetyl chloride (4.3 ml., 60 mM). The mixture was stirred at room temperature for 16 hr. The solvent was evaporated in vacuo and the residue was dissolved in a mixture of ethyl acetate (1 l.) and water (500 ml.). The mixture was separated and the organic phase was washed successively with water (500 ml.), 2N hydrochloric acid (2×500 ml.), water (500 ml.) and saturated brine (500 ml.). The organic phase was dried (Na2SO4) and the solvent evaporated in vacuo. The solid was crystallised from ethyl acetate/petroleum ether (b.p. 60°-80°) to give methyl 2-acetylamino-6-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylate, m.p. 160°-1°.

Provenance & Evidence