HCID 14923755, compound → 2,7-Dimethoxy-9H-carbazole
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[C:5]([N+:17]([O-])=O)[CH:4]=1>P(OCC)(OCC)OCC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[C:9]3[C:14](=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=3)[NH:17][C:5]=2[CH:4]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
The reaction was carried out in a vial. The crude biphenyl 10h (6.0 g) was dissolved in P(OEt)3 (36 mL). The vial was flushed with argon. The reaction mixture was heated to 90° C., kept at this temperature overnight, and cooled. As a result the carbazole precipitated. Et2O/CH2Cl2 mixture was added. The precipitate was filtered off and washed with CH2Cl2. The filtrate was evaporated. P(OEt)3 was added again, and the mixture was left for cyclization for 24 h. These operations were repeated until the precipitate formation ceased, and TLC indicated that the starting biphenyl disappeared. In total 2.9 g of the carbazole was obtained (65% calculated for two steps.)