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

HRID 51324Notes

Reaction equation

HRID 51324 reaction equation
[F: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>[F: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 227398669-[(3-Fluorophenyl)methyl]-2-methyl-4-hydroxy-5-carbomethoxy carbazole

Product 1

HCID 227400919-[(3-Fluorophenyl)methyl]-2-methyl-4-hydroxy-5-carbamoyl carbazoleYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the 9-[(3-fluorophenyl)methyl]-2-methyl-4-hydroxy-5-carbomethoxy carbazole (0.33 g, 0.91 mM) in 14 ml THF and 54 mL concentrated aqueous ammonium hydroxide was sonicated for 6.5 h at 30-40° C. The precipitated solid was filtered, washed with water, and triturated with 35 ml Et2O to afford 182 mg (57%) of 9-[(3-fluorophenyl)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), 7.25 (m, 1H), 7.05 (m, 1H), 6.9 (m, 2H), 6.85 (d, J=8 Hz, 1H), 6.45 (s, 1H), 5.65 (s, 2H), 2.4 (s, 3H). MS (ES) m/e 332, 349.

Workup

  1. filtrationThe precipitated solid was filtered
  2. washwashed with water
  3. customtriturated with 35 ml Et2O

Sources & evidence

ORD record
ord-9e33ce1412834e59a144a223fa0a1904
Source dataset
uspto-grants-2004_03
Patent number
US06713645B1

Reaction notes

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