Sulfuric Acid → 2-Benzylindan-2-ylamine
Reaction equation
[CH2:1]([C:8]1([NH:18]C(=O)C(F)(F)F)[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OS(O)(=O)=O>C(O)(=O)C>[CH2:1]([C:8]1([NH2:18])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of N-(2-benzyl-1-oxoindan-2-yl)-2,2,2-trifluoroacetamide (0.200 g, 0.60 mmol), 10% Pdl/C (50 mg) and concentrated H2SO4 (30 μl) in acetic acid (13.3 ml) is hydrogenated at 0.35 bar for 1 hour. Further concentrated H2SO4 (10 μl) is added and the hydrogenation is continued for 16 hours. The reaction is filtered, the filtrate is evaporated and the residue partitioned between ethyl acetate and water. The aqueous phase is basified to pH 11 with 1 M aqueous NaOH and extracted with ethyl acetate. The organic extract is washed with brine, dried (MgSO4) and evaporated to afford 2-benzylindan-2-ylamine, MH+ 224.