Sodium hydride → 4-Ethoxy-5-ethyl-2-nitroaniline

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Reaction Steps

N-(4-Ethoxy-5-ethyl-2-nitrophenyl)acetamide [0.2 g, Reference Example 32(g)] was dissolved in ethanol (25 mL) and sodium hydride (100 mg; 50% dispersion in mineral oil, 2 mmol) was added. Mixture was stirred overnight at ambient temperature, aq ammonium chloride (3mL) was added and the mixture was evaporated. The residue was chromatographed on silica gel (heptane with gradient of 25-50% ethyl acetate) to give 4-ethoxy-5-ethyl-2-nitrophenylamine (0.1 g) as a red solid. LC-MS (Method E): RT=3.4 minutes, 211 (M+H)+. (h) 5-Chloro-4-methoxy-2-nitrophenylamine

Provenance & Evidence