Ammonium Chloride → 3-Amino-4-chlorobenzaldehyde

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To a solution of 4-chloro-3-nitrobenzaldehyde 1 (11.47 g, 62 mmol) in MeOH (230 mL) and water (85 mL) was added ammonium chloride (24.2 g, 452 mmol) and iron (18.4 g, 329 mmol). The reaction mixture was stirred at room temperature for 16 h, filtered, partially concentrated under reduced pressure, and diluted with EtOAc and water. The aqueous phase was extracted with EtOAc (3×) and the combined organic extracts were washed with brine (1×), dried over MgSO4, filtered, and concentrated in vacuo. The crude aniline was dissolved in CH2Cl2 (˜150 mL), diluted with hexanes (˜300 mL), and cooled to 0° C. The solid was collected by filtration and washed with hexanes to give 3-amino-4-chlorobenzaldehyde 2 (5.36 g, 56% yield) as a yellow solid. Mass spectrum: calculated for C7H5ClNO 155.0. found 156.1 (M++1).

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