[C:1]([N:5]([CH3:15])[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=1)(=[O:4])[CH2:2][CH3:3]>C1COCC1.[Pd]>[C:1]([N:5]([CH3:15])[C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1)(=[O:4])[CH2:2][CH3:3]The reaction is carried out using an analogous method to (9b), using N-propionyl-N-methyl-4-nitroaniline (10a)(6.8 g, 32.86 mmol), 10%Pd on carbon (447 mg) in THF (75 ml). The hydrogenation yields an oil. ES+ (M+1) 178.87.
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