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Isolation of 3-amino-4-nitro-benzyl acetate: evidence of an undisclosed impurity in 5-amino-2-nitro-benzoic acid.


ABSTRACT: Yellow crystals of the title compound 3-amino-4-nitro-benzyl acetate, C9H10N2O4, were isolated from the reaction of acetic anhydride with (5-amino-2-nitro-phen-yl)methanol, prepared from reduction of commerically available 5-amino-2-nitro-benzoic acid with borane-THF. The mol-ecule is essentially planar (r.m.s. deviation = 0.028?Å). The mol-ecules are linked by inter-molecular N-H?O hydrogen-bonding inter-actions 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 ?-? inter-actions [centroid-centroid distances = 3.6240?(3) and 3.5855?(4)?Å]. A strong intra-molecular N-H?O hydrogen-bonding inter-action is observed between the nitro group and the amine group [2.660?(2)?Å].

SUBMITTER: Quillian B 

PROVIDER: S-EPMC4459301 | BioStudies | 2015-01-01

REPOSITORIES: biostudies

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