Ammonium Hydroxide → 9-[(Phenyl)methyl]-2-methyl-4-hydroxy-5-carbamoyl carbazole

HRID 567228Notes

Reaction equation

HRID 567228 reaction equation
[C:1]1([CH2:7][N:8]2[C:20]3[CH:19]=[C:18]([CH3:21])[CH:17]=[C:16]([OH:22])[C:15]=3[C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][C:13]=3[C:23]([O:25]C)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[NH4+:28]>C1COCC1>[C:1]1([CH2:7][N:8]2[C:20]3[CH:19]=[C:18]([CH3:21])[CH:17]=[C:16]([OH:22])[C:15]=3[C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][C:13]=3[C:23](=[O:25])[NH2:28])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 227397529-[(Phenyl)methyl]-2-methyl-4-hydroxy-5-carbomethoxy carbazole

Product 1

HCID 227393719-[(Phenyl)methyl]-2-methyl-4-hydroxy-5-carbamoyl carbazoleYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the 9-[(phenyl)methyl]-2-methyl-4-hydroxy-5-carbomethoxy carbazole (470 mg, 1.36 mM) in 20 ml THF and 80 mL concentrated aqueous ammonium hydroxide was sonicated for 6 hours at 30-40° C. The precipitated solid was filtered and triturated with Et2O to afford 200 mg (44%) of 9-[(phenyl)methyl]-2-methyl-4-hydroxy-5-carbamoyl carbazole. 1H NMR (DMSO-d6) δ 10.5 (s, 1H), 8.8 (bs, 1H), 8.4 (bs, 1H), 7.75 (m, 1H), 7.4 (m, 2H), 7.25 (m, 3H), 7.1 (m, 2H), 6.95 (s, 1H), 6.45 (s, 1H), 5.65 (s, 2H), 2.4 (s, 3H). MS (ES) m/e 314, 331.

Workup

  1. filtrationThe precipitated solid was filtered
  2. customtriturated with Et2O

Sources & evidence

ORD record
ord-9e1ba368089a465a9c3f3424ac1de67d
Source dataset
uspto-grants-2001_01
Patent number
US06177440B1

Reaction notes

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