Acetone → 5-(Hydroxymethyl)-11-methyl-6H-pyrido [4,3-b] carbazole N-Methylcarbamate

HRID 232182Notes

Reaction equation

HRID 232182 reaction equation
[OH:1][CH2:2][C:3]1[C:15]2[NH:14][C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:7]=2[C:6]([CH3:16])=[C:5]2[CH:17]=[N:18][CH:19]=[CH:20][C:4]=12.CC(C)=O.[CH3:25][N:26]=[C:27]=[O:28]>N1C=CC=CC=1>[CH3:25][NH:26][C:27](=[O:1])[OH:28].[OH:1][CH2:2][C:3]1[C:15]2[NH:14][C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:7]=2[C:6]([CH3:16])=[C:5]2[CH:17]=[N:18][CH:19]=[CH:20][C:4]=12

Participants

5

Reactant 3

HCID 180AcetoneHCID 12228Methyl IsocyanateHCID 3558146H-Pyrido(4,3-b)carbazole, 5-(hydroxymethyl)-11-methyl-

Product 1

HCID 211212325-(Hydroxymethyl)-11-methyl-6H-pyrido [4,3-b] carbazole N-Methylcarbamate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 400 mg (1.53 mmol) of the carbinol 25 in 25 mL of dry pyridine and 20 mL of reagent grade acetone there was added 900 uL of MeNCO. The solution was magnetically stirred at room temperature in a stoppered flask until all the starting alcohol had disappeared as judged by TLC (ca. 3 days). The solvents were removed in vacuo, and the residue was crystallized from EtOAc-CH2Cl2 -MeOH to give 152 mg of the desired carbamate, mp 213°-214.5° C. The filtrate was concentrated to dryness and the remaining solid was flash chromatographed to give an additional 145 mg of material of similar purity: wt 307 mg (61%); NMR (Me2SO-d6) 11.62 (s, 1 H), 9.71 (s, 1 H), 8.46 (d, 1 H), 839 (d, 1 H), 7.97 (d, 1 H), 7.61-7.54 (m, 2 H), 7.32-7.29 (m, 1 H), 7.04 (d, 1 H), 5.77 (s, 2 H), 3.34 (s, 3 H), 2.60 (s, 3 H).

Workup

  1. customas judged by TLC (ca. 3 days)
  2. customThe solvents were removed in vacuo
  3. customthe residue was crystallized from EtOAc-CH2Cl2 -MeOH

Sources & evidence

ORD record
ord-dd681125c2f44ee6bbbbaa90313801d4
Source dataset
uspto-grants-1989_07
Patent number
US04851417

Reaction notes

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