Hydrazine → 2-Amino-6-bromobenzenemethanol

HRID 459797Notes

Reaction equation

HRID 459797 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[C:3]=1[CH2:11][OH:12].NN>C1COCC1.CO.[Ni]>[NH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[C:3]=1[CH2:11][OH:12]

Participants

5

Reactant 2

HCID 9321HydrazineHCID 18444469(2-Bromo-6-nitrophenyl)methanol

Product 1

HCID 184444672-Amino-6-bromobenzenemethanolYield 84%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a warm solution of (2-bromo-6-nitro-phenyl)-methanol (751 mg, 3.24 mmol), and a catalytic amount of Raney (Ni) in THF/MeOH (10 ml/10 ml) was added H2NNH2 (0.2 ml, 6.37 mmol). With stirring, the solution was heated under reflux for an hour and was allowed to cool to room temperature. The reaction mixture was filtered through celite and washed with ethyl acetate. The concentrated filtrate was purified by flash chromatography to give (2-amino-6-bromo-phenyl)-methanol (549 mg, 84%). MS: 202.1 (M+H)+.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for an hour
  3. filtrationThe reaction mixture was filtered through celite
  4. washwashed with ethyl acetate
  5. customThe concentrated filtrate was purified by flash chromatography

Sources & evidence

ORD record
ord-0e2b9a5c7a7a424893e9f90badebceb5
Source dataset
uspto-grants-2007_03
Patent number
US07196087B2

Reaction notes

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