Ammonium formate → 1-N-(propan-2-yl)benzene-1,2-diamine
Reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[CH:10][C:5]=1[NH:6][CH:7]([CH3:9])[CH3:8])([O-])=O.C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH3:9][CH:7]([NH:6][C:5]1[C:4]([NH2:1])=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:8]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 2-nitro-N-(propan-2-yl)aniline (828 mg, 4.6 mmol) in ethanol (10 mL) under a nitrogen atmosphere is carefully added 20% palladium on carbon (50 mg, Degussa type) followed by ammonium formate (1.4 g, 23 mmol) and the reaction is stirred for 16 h. The suspension is carefully filtered through a bed of Celite and the filter cake is rinsed with additional ethanol (10 mL). The filtrate is concentrated and the residue is partitioned between H2O and ethyl acetate. The organic layer is dried (Na2SO4) and concentrated and the residue is purified by chromatography through a short bed of silica gel using 5% methanol/CH2Cl2 affords the title compound (552 mg, 80%) as an oil.