Water → 4-Bromo-2-nitroaniline

HRID 2093045Notes

Reaction equation

HRID 2093045 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]C(=O)C)=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1.O.[OH-].[K+]>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 14797Potassium HydroxideHCID 136690N-(4-bromo-2-nitrophenyl)acetamide

Product 1

HCID 701324-Bromo-2-nitroanilineYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(4-bromo-2-nitrophenyl)acetamide obtained in step H above (1.0 eq) in MeOH and water was added KOH (1.5 eq) at room temperature and stirred for 5 hrs. Water was added to the reaction mixture and the organic layer was separated, dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford crude product, which, on purification by column chromatography afforded the desired 4-bromo-2-nitroaniline. (Yield=95%)

Workup

  1. customthe organic layer was separated
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customto afford crude product, which
  5. customon purification by column chromatography

Sources & evidence

ORD record
ord-26db4a7f79844a6789453d0b1344a46b
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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