Acetone → N-Methylcarbazole

HRID 638521Notes

Reaction equation

HRID 638521 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[CH3:16]C(C)=O>S([O-])(OC)(=O)=O.O>[CH3:16][N:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2

Participants

6

Reactant 3

HCID 180AcetoneHCID 6854CarbazoleHCID 14798Sodium Hydroxide

Product 1

HCID 15142N-MethylcarbazoleYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 4694097Methyl sulfate(1-)Solvent

Procedure

To a vigourously stirred solution of 10 g of carbazole in 50 ml of acetone, 10 ml methyl sulphate was added, followed by dropwise addition of a solution of 10 g NaOH in 7 ml water. After a few minutes the solution was poured into water. N-methyl carbazole was purified by two ethanol recrystallization, extraction with boiling petroleum ether and another ethanol recrystallization (yield 90% m.p.=88° C.).

Workup

  1. customN-methyl carbazole was purified by two ethanol recrystallization, extraction with boiling petroleum ether
  2. customanother ethanol recrystallization (yield 90% m.p.=88° C.)

Sources & evidence

ORD record
ord-dbd95565ba8f41bfba74efab74af9a0c
Source dataset
uspto-grants-1985_12
Patent number
US04562133

Reaction notes

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