2-Benzyl-1,1,3,3-tetramethylisoindoline → 1,1,3,3-Tetramethylisoindoline
Reaction equation
C([N:8]1[C:16]([CH3:18])([CH3:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1([CH3:20])[CH3:19])C1C=CC=CC=1>C(O)(=O)C.[Pd]>[CH3:17][C:16]1([CH3:18])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH3:20])([CH3:19])[NH:8]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 2-benzyl-1,1,3,3,-tetramethylisoindoline (5.5 g 20 mmol) in glacial acetic acid (20 ml) was hydrogenated at 60 lb/in2 over 5% palladium/c for 3 h at room temperature. The suspension was filtered and the solvent removed at reduced pressure. The residue was dissolved in water and the solution was made alkaline (PH 9) by the addition of 10% sodium hydroxide and extracted with ether (3×50 ml). The combined organic extracts were dried and evaporated to dryness to give the title compound (3.5 g 96%), which was recrystalized from methanol/water. m.p. 36-38° C. NMR (CDCl3, 400 MHz), 1.46 s, 4 x CH3; 1.9 s, NH, D2O exchanged; 7.1-7.27 m, ArH.