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

HRID 525272Notes

Reaction equation

HRID 525272 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-7456ef521d42470b93e9219ab369fecb
Source dataset
uspto-grants-2016_05
Patent number
US09340557B2

Reaction notes

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