N-(4-acetyl-3-hydroxy-2-nitrophenyl)acetaMide synthesis

Yield:-

Reaction Conditions:

with nitric acid;acetic anhydride in dichloromethane;

Steps:

N-(4-Acetyl-3-hydroxy-2-nitrophenyl)acetamide

N-(4-Acetyl-3-hydroxy-2-nitrophenyl)acetamide A mixture of N-(4-acetyl-3-hydroxyphenyl)acetamide (9.66 g, 50 mmol) and acetic anhydride (14.2 ml, 15.3 g, 150 mmol) in dichloromethane (150 ml) was cooled to 5° C. and nitric acid (90%, d 1.49, 4.70 ml, 7.00 g, 100 mmol) was added dropwise. The mixture was stirred at room temperature for 1 hour, poured into water (150 ml) and extracted with dichloromethane (3*150 ml). The combined organic fractions were dried (Na₂ SO₄) and evaporated under reduced pressure and the residue was purified by repeated flash column chromatography on silica gel, eluding with hexane/30% ethyl acetate then hexane/50% ethyl acetate. The first isomer to elute was N-(4-acetyl-5-hydroxy-2-nitrophenyl)acetamide as a yellow solid (3.87 g, 33%). ¹ H NMR (CDCl₃): δ12.83 (1H, s), 10.78 (1H, br s), 8.78 (1H, s), 8.43 (1H, s), 2.68 (3H, s), 2.32 (3H, s).

References:

US5206240,1993,A