Water → 4-Isopropyl-2-nitroaniline

HRID 2093039Notes

Reaction equation

HRID 2093039 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10]C(=O)C)=[C:6]([N+:14]([O-:16])=[O:15])[CH:5]=1)([CH3:3])[CH3:2].O.[OH-].[K+]>CO>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([N+:14]([O-:16])=[O:15])[CH:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962Water2×HCID 14797Potassium HydroxideHCID 4200165N-(4-isopropyl-2-nitrophenyl)acetamide

Product 1

HCID 27366964-Isopropyl-2-nitroanilineYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(4-isopropyl-2-nitrophenyl)acetamide obtained in step II 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-isopropyl-2-nitroaniline. (Yield=65%).

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-4234ba66bd914b4fbc157bc7805b1ac9
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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