[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:35][C:36]1[CH:37]=[C:38]([CH:40]=[CH:41][C:42]=1[CH3:43])[NH2:39]>CN(C=O)C.CCOC(C)=O.O>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:39][C:38]2[CH:40]=[CH:41][C:42]([CH3:43])=[C:36]([CH3:35])[CH:37]=2)=[O:8])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]To a solution of 4-amino-3-nitro-benzoic acid (546 mg). EDCI (576 mg) and HOBt (405 mg) in DMF (8 mL) was added 3,4-dimethylaniline (363 mg) and the mixture was stirred at room temperature for 3 h. The mixture was poured into water and exreacted with EtOAc. The organic phase was washed with water (2×) and was dried over sodium sulfate. The solvent was concentrated to approximately 10 mL and the resulting precipitate was filtered, washed with EtOAc and dried under reduced pressure to give 4-amino-N-(3,4-dimethyl-phenyl)-3-nitro-benzamide as a yellow solid, mp=192-195° C.; MS (m/z) 284 (M−1).
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