Phenylacetyl chloride → N-(Benzylcarbonyl)-5-chloro-2-hydroxymethylaniline

Participants

Reaction Conditions

Reaction Steps

To a suspension of 5-chloro-2-hydroxymethyl aniline (8.00 g) in dichloromethane (400 ml) under nitrogen at room temperature, was added triethylamine (15.6 ml). The reaction mixture was cooled to 0° C. then phenyl acetyl chloride (14.80 ml) was added dropwise over 10 mins, and the reaction mixture was allowed to warm to room temperature and stir for 2 h. The mixture was washed with 1N HCl (2×250 ml) and brine (1×250 ml). The aqueous layers were re-extracted using CH2Cl2 (1×250 ml) and the combined organic layers were dried (MgSO4), filtered and the solvent was removed under vacuum to leave an orange solid. The solid was suspended in MeOH (400 ml), sodium hydroxide (2.20 g) was added in water (100 ml) and the reaction mixture was allowed to stir under gentle heating (50° C.) for 45 mins. The methanol was removed in vacuo, then the aqueous residue was extracted with dichloromethane (1×200 ml) and the organic layer was washed with brine (1×150 ml) and saturated sodium hydrogen carbonate solution (1×150 ml). The organic layer was dried (MgSO4), filtered and the solvent was removed under vacuum to leave a solid. Trituration with diethyl ether gave the required compound (10.00 g).

Provenance & Evidence