2-Bromo-4-methoxy-6-nitrophenol → 2-Amino-6-Bromo-4-Methoxyphenol

HRID 858231Notes

Reaction equation

HRID 858231 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([N+:10]([O-])=O)[C:3]=1[OH:13]>CCOC(C)=O.[Ni]>[NH2:10][C:4]1[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=[C:2]([Br:1])[C:3]=1[OH:13]

Participants

4

Reactant 1

HCID 112651402-Bromo-4-methoxy-6-nitrophenol

Product 1

HCID 111719822-Amino-6-Bromo-4-MethoxyphenolYield 96%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Raney/Ni (2.5 g) was added into a solution of 2-bromo-4-methoxy-6-nitrophenol (8.8 g, 35.5 mmol) in EtOAc (100 mL). The mixture was shaken in a Parr apparatus under hydrogen at 25 psi for 2.5 h. The reaction mixture was filtered through celite and concentrated under vacuum to give a gray solid (7.4 g, 96% yield; 95–97° C.); MS m/e 218 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationconcentrated under vacuum
  3. customto give a gray solid (7.4 g, 96% yield; 95–97° C.)

Sources & evidence

ORD record
ord-e4b74141cccb4562b03f434628c030af
Source dataset
uspto-grants-2006_12
Patent number
US07148247B2

Reaction notes

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