4-chloro-3-[(dimethylamino)methyl]aniline

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Iron (1.36 g, 21.9 mmol) and concentrated hydrochloric acid (0.15 mL) was added to ethanol/water (20 mL/20 mL), followed by refluxing for 1 hour. The mixed reaction solution was added with 1-(2-chloro-5-nitrophenyl)-N,N-dimethylmethanamine (940 mg, 4.38 mmol) obtained in <Step 1> above, and refluxed for 1 hour. The reaction mixture was filtered through a Celite pad under reduced pressure, and washed with ethanol and chloroform/2-propanol=3/1 (v/v). The resulting filtrate was distilled under reduced pressure, and dissolved in ethyl acetate. The organic layer formed was washed with an aqueous solution of sodium bicarbonate and brine. The obtained organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The concentrated compound was purified using silica gel chromatography (chloroform:methanol=30:1→15:1 (v/v)) to obtain the title compound (442 mg, 55%). by refluxing for 1 hour The mixed reaction solution obtained in <Step 1> above, and refluxed for 1 hour The reaction mixture was filtered through a Celite pad under reduced pressure washed with ethanol and chloroform/2-propanol=3/1 (v/v) The resulting filtrate was distilled under reduced pressure dissolved in ethyl acetate The organic layer formed was washed with an aqueous solution of sodium bicarbonate and brine The obtained organic layer was dried over anhydrous sodium sulfate filtered concentrated under reduced pressure The concentrated compound was purified