[OH-].[Na+].[CH3:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[C:11]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-])=O)[C:12]=1[C:13]([NH:15][CH3:16])=[O:14]>O.CO.[Zn]>[CH3:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[C:11]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:12]=1[C:13](=[O:14])[N:15]([CH3:16])[NH:21]2A solution of sodium hydroxide (0.035 g, 0.88 mmol) in water (2 ml) was added to a solution containing 0.095 g (0.33 mmol) of 2-(2,4-dimethylphenyl)-N-methyl-6-nitrobenzamide in methanol (1.5 ml). Zinc powder (0.03 g, 0.44 mmol) was then added to the mixture, which was heated under reflux for 24 h. After cooling, the zinc residue was separated by filtration and the methanol was partially evaporated. The residual solution was then adjusted to pH 7 with aqueous hydrochloric acid. The mixture was diluted with ethyl acetate and washed with saturated sodium bicarbonate. The organic phase was dried over magnesium sulfate. Filtration, removal of solvent and purification of the residue via biotage eluting with 40% ethyl acetate/hexanes gave 0.01 g (22%) of product.
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