[N+:1]([C:4]1[CH:22]=[CH:21][C:7]([C:8]([N:10]([CH3:20])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:17][CH2:18][OH:19])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.C1C=CC=CC=1.C[Si](C=[N+]=[N-])(C)C.CN(C)[CH:59]=[O:60]>O.CO>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([N:10]([CH3:20])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:17][C:18]([O:60][CH3:59])=[O:19])=[O:9])=[CH:21][CH:22]=1)([O-:3])=[O:2]
To a solution of 4-nitro-N-methyl-N-[2-(2-hydroxyethyl)phenyl]benzamide (686 mg) in N,N-dimethylformamide (12 ml) was added pyridinium dichromate (4.3 g) and the mixture was stirred at ambient temperature for 2 days. The mixture was diluted with water (80 ml) and the aqueous solution was extracted with ethyl acetate. The extract was washed with brine and dried over magnesium sulfate. Filtering and removal of solvents afforded a brown oil. To a solution of the brown oil in methanol (3 ml) and benzene (11 ml) was added trimethylsilyl diazomethane (1.7 ml) and the resulting solution was stirred at ambient temperature for 30 minutes. The mixture was evaporated in vacuo to give 4-nitro-N-methyl-N-(2-methoxycarbonylmethylphenyl)benzamide (517 mg) as a dark-green oil.
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