Acetone → 9-methoxy-5-hydroxymethyl-11-methyl-6H-pyrido [4, 3-b] carbazole N-methyl carbamate

HRID 232183Notes

Reaction equation

HRID 232183 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:13]2[NH:12][C:11]3[C:10]([CH2:16][OH:17])=[C:9]4[CH:18]=[CH:19][N:20]=[CH:21][C:8]4=[C:7]([CH3:22])[C:6]=3[C:5]=2[CH:4]=1.CC(C)=O.[CH3:27][N:28]=[C:29]=[O:30].OCC1C2NC3C=CC=CC=3C=2C(C)=C2C=NC=CC=12>N1C=CC=CC=1>[CH3:27][NH:28][C:29](=[O:2])[OH:30].[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:13]2[NH:12][C:11]3[C:10]([CH2:16][OH:17])=[C:9]4[CH:18]=[CH:19][N:20]=[CH:21][C:8]4=[C:7]([CH3:22])[C:6]=3[C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 12228Methyl IsocyanateHCID 3558146H-Pyrido(4,3-b)carbazole, 5-(hydroxymethyl)-11-methyl-HCID 145761239-Methoxy-5-hydroxymethyl-11-methyl-6H-pyrido [4,3-b] carbazole2×

Product 1

HCID 867432629-methoxy-5-hydroxymethyl-11-methyl-6H-pyrido [4, 3-b] carbazole N-methyl carbamate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The above alcohol 36 was dissolved in dry pyridine and dry acetone and treated with methyl isocyanate as in the case of the carbinol 25. The mixture was stirred until no further alcohol 36 could be detected on thin layer chromatography. The solvents were evaporated and the residual solid was crystallized from ethyl acetate-methanol to give the desired carbamate 37.

Workup

  1. customThe solvents were evaporated
  2. customthe residual solid was crystallized from ethyl acetate-methanol

Sources & evidence

ORD record
ord-4473e82197a04688a0471ed3a8bee759
Source dataset
uspto-grants-1989_07
Patent number
US04851417

Reaction notes

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