C(Cl)(=O)C(Cl)=O.[C:7]([O:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=1)(=[O:9])[CH3:8].[CH3:20][C:21]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][C:22]=1[NH2:23].N1C=CC=CC=1>CN(C=O)C.C(Cl)Cl>[CH3:20][C:21]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][C:22]=1[NH:23][C:15](=[O:17])[C:14]1[CH:13]=[CH:12][C:11]([O:10][C:7](=[O:9])[CH3:8])=[CH:19][CH:18]=1Oxalyl chloride (0.5 ml) was added slowly to a stirred mixture of 4-acetoxybenzoic acid (1.09 g), methylene chloride (30 ml) and DMF (one drop) and the mixture was stirred at ambient temperature for 2 hours. A solution of 2-methyl-5-nitroaniline (0.76 g) and pyridine (2 ml) in methylene chloride was added over 15 minutes and the mixture was stirred for a further 2 hours. The reaction mixture washed with a 5% aqueous acetic acid solution, with water and with a 5% aqueous sodium bicarbonate solution. The organic extract was dried (MgSO4) and evaporated. The residue was recrystallised from ethyl acetate to give N-(2-methyl-5-nitrophenyl)-4-acetoxybenzamide (0.8 g), m.p. 207-208° C.; NMR Spectrum: (DMSOd6) 2.3 (s, 3H), 7.31 (d, 2H), 7.56 (d, 1H), 8.02 (m, 3H), 8.47 (d, 1H), 10.12 (s, 1H).
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