Ammonium Hydroxide → 9-[(2,6-Dichlorophenyl)methyl]-4-hydroxy-5-carbamoyl carbazole

HRID 51425Notes

Reaction equation

HRID 51425 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][N:10]1[C:22]2[CH:21]=[CH:20][CH:19]=[C:18]([OH:23])[C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][C:15]=2[C:24]([O:26]C)=O.[OH-].[NH4+:29]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][N:10]1[C:22]2[CH:21]=[CH:20][CH:19]=[C:18]([OH:23])[C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][C:15]=2[C:24](=[O:26])[NH2:29]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 22738600HCID 22738600, compound

Product 1

HCID 227386829-[(2,6-Dichlorophenyl)methyl]-4-hydroxy-5-carbamoyl carbazoleYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the 9-[(2,6-dichlorophenyl)methyl]-4-hydroxy-5-carbomethoxy carbazole (240 mg, 0.6 mM) in 5 mL THF and 20 mL concentrated aqueous ammonium hydroxide was stirred at room temperature for 22 hours. The resultant precipitate was collected by filtration and dried in vacuo to afford 151 mg (65%) of the 9-[(2,6-dichlorophenyl)methyl]-4-hydroxy-5-carbamoyl carbazole as a yellow solid. 1H NMR (DMSO-d6) δ10.35 (s, 1H), 8.8 (br s, 1H), 8.4 (br s, 1H), 7.7 (d, 1H, J=8 Hz), 7.6-7.3 (m, 5H), 7.25 (t, 1H, J=8 Hz), 6.85 (d, 1H, J=8 Hz), 6.55 (d, 1H, J=8 Hz), and 5.85 (s, 2H). IR (KBr, cm−1) 3429, 1631, and 1597. MS (ES) m/e 385, 387.

Workup

  1. filtrationThe resultant precipitate was collected by filtration
  2. customdried in vacuo

Sources & evidence

ORD record
ord-7121dab55f944717bdfd95da5b986b18
Source dataset
uspto-grants-2004_03
Patent number
US06713645B1

Reaction notes

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