Ammonium Hydroxide → 9-[(3-Methylphenyl)methyl]-2-methyl-4-hydroxy-5-carbamoyl carbazole

HRID 51329Notes

Reaction equation

HRID 51329 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:8][N:9]2[C:21]3[CH:20]=[C:19]([CH3:22])[CH:18]=[C:17]([OH:23])[C:16]=3[C:15]3[C:10]2=[CH:11][CH:12]=[CH:13][C:14]=3[C:24]([O:26]C)=O)[CH:5]=[CH:6][CH:7]=1.[OH-].[NH4+:29]>C1COCC1>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:8][N:9]2[C:21]3[CH:20]=[C:19]([CH3:22])[CH:18]=[C:17]([OH:23])[C:16]=3[C:15]3[C:10]2=[CH:11][CH:12]=[CH:13][C:14]=3[C:24](=[O:26])[NH2:29])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 227381449-[(3-Methylphenyl)methyl]-2-methyl-4-hydroxy-5-carbomethoxy carbazole

Product 1

HCID 227401829-[(3-Methylphenyl)methyl]-2-methyl-4-hydroxy-5-carbamoyl carbazoleYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 9-[(3-methylphenyl)methyl]-2-methyl-4-hydroxy-5-carbomethoxy carbazole (0.92 g, 2.56 mM) in 38 ml THF and 154 mL concentrated aqueous ammonium hydroxide was sonicated for 6 h at 30-40° C. The precipitated solid was filtered, washed with water to afford 0.55 g (63%) of 9-[(3-methylphenyl)methyl]-2-methyl-4-hydroxy-5-carbamoyl carbazole. 1H NMR (DMSO-d6) δ10.5 (s, 1H), 8.8 (bs, 1H), 8.4 (bs, 1H), 7.75 (m, 1H), 7.4 (m, 2H), 7.15 (dd, J=8 and 8 Hz, 1H), 7.05 (m, 1H), 7.0 (s, 1H), 6.9 (s, 1H), 6.8 (d, J=8 Hz, 1H), 6.45 (s, 1H), 5.65 (s, 2H), 2.4 (s, 3H)., 2.2 (s, 3H). MS (ES) m/e 328, 345.

Workup

  1. filtrationThe precipitated solid was filtered
  2. washwashed with water

Sources & evidence

ORD record
ord-732999cc6d5040cab43eca573d58a553
Source dataset
uspto-grants-2004_03
Patent number
US06713645B1

Reaction notes

Loading…