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

HRID 567336Notes

Reaction equation

HRID 567336 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) δ 10.35 (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-caaacfecde014f09b31c96536819c998
Source dataset
uspto-grants-2001_01
Patent number
US06177440B1

Reaction notes

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