2-Amino-5-bromo-3-nitrophenol → 2,3-Diamino-5-bromophenol

HRID 2200770Notes

Reaction equation

HRID 2200770 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([Br:11])=[CH:4][C:3]=1[OH:12]>C(OCC)(=O)C.[Ni]>[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([Br:11])=[CH:4][C:3]=1[OH:12]

Participants

4

Reactant 1

HCID 598378212-Amino-5-bromo-3-nitrophenol

Product 1

HCID 892699422,3-Diamino-5-bromophenol

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

As shown in step 6-iv of Scheme 6, to a solution of 2-amino-5-bromo-3-nitrophenol (7.5 g, 31.8 mmol) in ethyl acetate (60 mL) was added Raney Nickel™ (1.90 g, 214 μL, 32.4 mmol) and the reaction mixture was shaken for 2 hours under an atmosphere of H2 at 30 p.s.i. After filtering and drying over Na2SO4, the mixture was concentrated under reduced pressure to provide 2,3-diamino-5-bromophenol (compound 1016), which was used as is in subsequent reactions without further purification.

Workup

  1. filtrationAfter filtering
  2. dry with materialdrying over Na2SO4
  3. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1d4c8ec5737d4197b7ee043364cf1b3d
Source dataset
uspto-grants-2016_06
Patent number
US09359380B2

Reaction notes

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