N-(t-butylphenyl) carbazolone → N-(t-butylphenyl)hydroxycarbazole
Reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[C:23]2[C:22](=[O:24])[CH2:21][CH:20]=[CH:19][C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2)([CH3:4])([CH3:3])[CH3:2]>[Pd].C1(OC2C=CC=CC=2)C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[C:23]2[C:22]([OH:24])=[CH:21][CH:20]=[CH:19][C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2)([CH3:4])([CH3:2])[CH3:3]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
In a 500 ml two-neck flask, N-(t-butylphenyl) carbazolone (Compound F, 13 g) and diphenylether (100 ml) were mixed, and the 10% Pd/C (13 g) was added thereto. This reaction solution was refluxed and stirred for 30 minutes to 1 hour. When the reaction was completed, 80% of diphenylether was removed by distillation under reduced pressure, and a catalyst was removed using celite. The filtrate was washed again with ethylacetate. The filtrate was concentrated under reduced pressure and separated using a column chromatography, thereby obtaining 11 g of N-(t-butylphenyl)hydroxycarbazole (Compound G).