Hydrochloric Acid → 2-Chloro-5-methylaniline

Participants

Reaction Steps

To a solution of 1-chloro-4-methyl-2-nitrobenzene (10.0 g, 0.058 mol) in methanol (50 mL), iron powder (3.0 g, 0.055 mol) and conc. HCl (10 mL) were added. The reaction mixture was stirred at RT for 2 h. The reaction mixture was diluted with water and basified with NaHCO3 solution and extracted with DCM. The organic layer was separated and dried over anhydrous sodium sulphate and concentrated to afford 5.0 g of the desired compound. 1HNMR (CDCl3): δ 2.23 (s, 3H), 3.94 (s, 2H), 6.50 (d, J=7.8 Hz, 1H), 6.57 (s, 1H), 7.10 (d, J=7.8 Hz, 1H); MS [M+H]+: 142.25.

Provenance & Evidence