Hydrochloric Acid → 1-(4-Amino-5-chloro-2-methoxyphenyl)ethan-1-one

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Reaction Conditions

Reaction Steps

N-Methoxy-N-methyl-4-amino-5-chloro-2-methoxybenzamide (24.4 g, 100 mmol) was dissolved in THF (400 mL) and the solution was cooled to -400° C. Methyl-lithium in ether (143 mL, 4.4 g, 200 mmol) ) was added and the mixture was allowed to warm to 0° C. Aqueous hydrochloric acid was added and the mixture was extracted into ethyl acetate. The extract was washed with brine, dried over sodium sulfate, and evaporated to leave a solid. Crystallization from ethyl acetate-hexane gave 4'-amino-5'-chloro-2'-methoxyacetophenone (15.0 g, 75 mmol), m.p. 114°-116° C.

Provenance & Evidence