Isolation of 3-amino-4-nitro­benzyl acetate: evidence of an undisclosed impurity in 5-amino-2-nitro­benzoic acid

Yellow crystals of the title compound 3-amino-4-nitro­benzyl acetate, C(9)H(10)N(2)O(4), were isolated from the reaction of acetic anhydride with (5-amino-2-nitro­phen­yl)methanol, prepared from reduction of commerically available 5-amino-2-nitro­benzoic acid with borane–THF. The mol­ecule is essentially planar (r.m.s. deviation = 0.028 Å). The mol­ecules are linked by inter­molecular N—H⋯O hydrogen-bonding inter­actions between the carbonyl and amine groups, forming a zigzag chain along the b-axis direction lying in a plane parallel to (-102). The chains are stacked along the c axis by π–π inter­actions [centroid–centroid distances = 3.6240 (3) and 3.5855 (4) Å]. A strong intra­molecular N—H⋯O hydrogen-bonding inter­action is observed between the nitro group and the amine group [2.660 (2) Å].