Aniline → 2-chloro-N-(2-methoxy-4-nitrophenyl)acetamide

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Reaction Conditions

Reaction Steps

2-Methoxy-4-nitroaniline (8.40 g, 50 mmol) was dissolved in 200 mL dichloromethane and stirred at 0° C. while adding diisopropylethylamine (6.45 g, 50 mmol) then a solution of chloroacetyl chloride (5.65 g, 50 mmol) in 50 mL dichloromethane. The mixture was stirred for 17 h at 20-25° C., evaporated and 300 mL ethyl acetate added. The solution was washed with 2×100 mL 2M hydrochloric acid then brine, dried (sodium sulphate) and evaporated. The residue dissolved in 200 mL warm toluene, charcoaled then chromatographed on 300 mL flash silica in a 10 cm sinter funnel. Elution with toluene and evaporation afforded a bright yellow oil which solidified on standing. NMR showed an 11:4 mixture of product and starting aniline—product δ 9.17(s, 1H), 8.56(m,1H), 7.94(m, 1H), 7.79(m, 1H), 4.22(s, 2H), 4.03(s, 3H). Used without further purification.

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