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With nitric acid; acetic anhydride; In dichloromethane;
Example 6 Preparation of 4-Acetoxy-2-nitroacetanilide (V) A 500 mL, Erlenmeyer flask equipped with a magnetic stirring bar and a thermocouple was charged with <strong>[2623-33-8]4-acetoxyacetanilide</strong> (10.3 g, 0.05 mol), methylene chloride (50 mL), and acetic anhydride (16.2 g, 0.16 mol). The mixture was stirred at ambient temperature for 15 minutes (incomplete solution), and then was cooled to 0C (ice-salt bath). Nitric acid (5.0 mL, 0.08 mol, 70% acid, d=1.42) was added over a 30 second period. The ice bath was removed and the mixture was heated to boiling (42.5C) and maintained at that temperature for 30 minutes. The reaction temperature was slowly increased to 75C to distill methylene chloride, and then the mixture was allowed to cool slowly to ambient temperature and stand for 16 hours. The crystalline precipitate was isolated by filtration and vacuum dried to yield 7.1 g, 0.03 mol of 4-acetoxy-2-nitroacetanilide (mp 143-146C).