Acetone → N-Methylcarbazole

HRID 1658106Notes

Reaction equation

HRID 1658106 reaction equation
[CH3:1]C(C)=O.[CH:5]1[C:17]2[NH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[CH:8]=[CH:7][CH:6]=1.S([O-])(OC)(=O)=O.[OH-].[Na+]>O>[CH3:1][N:16]1[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]2[C:17]1=[CH:5][CH:6]=[CH:7][CH:8]=2

Participants

6

Reactant 4

HCID 180AcetoneHCID 6854CarbazoleHCID 14798Sodium HydroxideHCID 4694097Methyl sulfate(1-)

Product 1

HCID 15142N-Methylcarbazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The 9-substituted lower alkyl carbazoles are obtained in almost quantitative yield by the action of a concentrated aqueous solution of sodium or potassium hydroxide upon an acetone solution of carbazole using an appropriate lower alkyl iodide or sulfate. Thus, for example, when an acetone solution of carbazole and methyl sulfate is mixed with an aqueous solution of sodium hydroxide, vigorously shaken and poured into water, an almost quantitative yield of N-methylcarbazole is obtained.

Sources & evidence

ORD record
ord-e235171aa5bf44af98b6a68b9a68a61c
Source dataset
uspto-grants-1976_06
Patent number
US03962451

Reaction notes

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