Water → Methyl 3-amino-5-chloro-2-methylbenzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 5-chloro-2-methyl-3-nitrobenzoate (9.19 g, 40 mmol) in methanol (200 ml) at room temperature was added ammonium chloride (21 g, 400 mmol) followed by deionized water (100 ml). The mixture was heated to 70° C. before the addition of iron (13.4 g, 240 mmol). The reaction turned to a dark colour over the 2.5 hours it was stirred at 70° C. This mixture was allowed to cool to room temperature and was filtered through Kieselgel. The filter pad was washed with MeOH (100 ml) and the filtrate concentrated under reduced pressure. The residue was dissolved in deionized water (100 ml) and EtOAc (100 ml). The phases were separated and the aqueous phase was extracted with EtOAc (2×100 ml). The combined organic extracts were washed with brine (100 ml), dried over MgSO4, filtered and concentrated under reduced pressure to give 7.6 g of the title compound as a viscous orange oil that solidified upon standing. This material was used without further purification. LC-MS 63%, m/z=200.3/202.0, 1H NMR (500 MHz, Chloroform-d) δ 7.20 (1H, d, J=2.21 Hz), 6.80 (1H, d, J=2.05 Hz), 3.89 (3H, s), 3.74-3.87 (2H, m), 2.30 (3H, s).

Provenance & Evidence