2,4-Dinitrobenzoic acid → 2,4-Dinitrobenzamide

HRID 235060

Reaction equation

[N+:1]([C:4]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:5]=1[C:6](O)=[O:7])([O-:3])=[O:2].C(Cl)(=O)C(Cl)=O.[NH4+:22].[OH-]>>[N+:1]([C:4]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:5]=1[C:6]([NH2:22])=[O:7])([O-:3])=[O:2]

Participants

Reactant 3

HCID 118802,4-Dinitrobenzoic acid

HCID 14923Ammonium Hydroxide

HCID 65578Oxalyl chloride

Product 1

HCID 37335182,4-DinitrobenzamideYield 89%

Procedure

2,4-Dinitrobenzoic acid (8.17 g, 38.5 mmol) was treated with oxalyl chloride (3.90 mL, 44.7 mmol). The resulting acid chloride was treated with saturated NH4OH solution (200 mL) to yield the title compound (7.25 g, 89%). m.p. 202°-204° C. 1H NMR (300 MHz, DMSO) δ8.75 (d, 1H), 8.58 (dd, 1H), 8.48 (br s, 1H), 7.99 (br s, 1H), 7.91 (d, 1H), 5.50-6.20 (br s, 2H). MS (DCI/NH3) m/e 229 (M+NH4)+.

Sources & evidence

ORD record: ord-31a6f5a7f71c4d809ae281e01e1ca844
Source dataset: uspto-grants-1997_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05597823

Linked notes

Loading…