Sodium Hydroxide → 1-Fluoro-9-(2-aminophenyl)-9H-carbazole

HRID 2277356Notes

Reaction equation

HRID 2277356 reaction equation
[F:1][C:2]1[C:14]2[N:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N+:21]([O-])=O)[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CCO.[Cl-].[Cl-].[Zn+2]>[F:1][C:2]1[C:14]2[N:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[NH2:21])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67324830fluoro-9-(2-nitrophenyl)-9H-carbazole

Product 1

HCID 673252571-Fluoro-9-(2-aminophenyl)-9H-carbazole

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 702EthanolSolvent

Procedure

50 g (163 mmol) of 1-fluoro-9-(2-nitrophenyl)-9H-carbazole are dissolved in 600 ml of EtOH, 67 g (489 mmol) of ZnCl2 are added at room temperature, and the mixture is heated under reflux for 6 h. The mixture is subsequently warmed to room temperature over the course of 1 h, 20% NaOH is added, and, after phase separation, the solvent is removed, and the residue is purified by chromatography.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 6 h
  3. additionis added
  4. customafter phase separation
  5. customthe solvent is removed
  6. customthe residue is purified by chromatography

Sources & evidence

ORD record
ord-4d323738e3a647509f8f85eeef821c4d
Source dataset
uspto-grants-2015_09
Patent number
US09133119B2

Reaction notes

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