HCID 14923755, compound → 2,7-Dimethoxy-9H-carbazole

HRID 1614998Notes

Reaction equation

HRID 1614998 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]=1

Participants

3

Reactant 1

HCID 14923755HCID 14923755, compound

Product 1

HCID 123393992,7-Dimethoxy-9H-carbazole

Reagents, catalysts & solvents 1

HCID 31215Triethyl phosphiteSolvent

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.)

Workup

  1. customThe vial was flushed with argon
  2. customkept at this temperature overnight
  3. temperaturecooled

Sources & evidence

ORD record
ord-8a367792293a49bdbf636b3d2b756b21
Source dataset
uspto-grants-2014_07
Patent number
US08765738B2

Reaction notes

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