Methyl 4-acetamido-3-iodobenzoate → N-(4-(Hydroxymethyl)-2-iodophenyl)acetamide

Participants

Reaction Conditions

Reaction Steps

Lithium aluminium hydride (2.43 g, 64.1 mmol) was taken in a dry, three-necked, round bottom flask. Anhydrous THF (80 mL) was added and cooled to −10° C. A solution of 4-acetylamino-3-iodo-benzoic acid methyl ester (10.2 g, 32.0 mmol) in anhydrous THF (60 mL) was added dropwise at −10° C. over a period of 45 minutes under nitrogen. Stirring was continued at −10° C. for 1 hour. The reaction mixture was quenched with saturated sodium sulfate aqueous solution. The reaction mixture was then filtered, and the filtrate was concentrated. The solid was washed with methanol. The combined organic phases were dried over anhydrous Na2SO4. The solvent was evaporated. The crude compound was purified by the Simpliflash system (5% methanol in CH2Cl2 as eluent), to give N-(4-hydroxymethyl-2-iodo-phenyl)-acetamide as a white solid. Yield: 6.36 g (68%).

Provenance & Evidence