[CH3:1][N:2]([C:12](=[O:14])[CH3:13])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-])=O)[CH:4]=1>CO.O1CCOCC1.[C].[Pd]>[NH2:9][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[N:2]([CH3:1])[C:12](=[O:14])[CH3:13]A mixture of N-methyl-3′-nitroacetanilide (5.13 g) and 10% palladium carbon (0.6 g) in methanol (50 ml) and 1,4-dioxane (50 ml) and stirred under hydrogen (3 atm) at room temperature for 2 hours. The catalyst was removed by filtration and the solvent was evaporated. The resultant solid was collected and washed with isopropyl ether to give 3′-amino-N-methylacetanilide (4.06 g).
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