Water → 4-Amino-N,N-dimethyl-3-nitroaniline

HRID 2093042Notes

Reaction equation

HRID 2093042 reaction equation
[CH3:1][N:2]([CH3:16])[C:3]1[CH:8]=[CH:7][C:6]([NH:9]C(=O)C)=[C:5]([N+:13]([O-:15])=[O:14])[CH:4]=1.O.[OH-].[K+]>CO>[NH2:9][C:6]1[CH:7]=[CH:8][C:3]([N:2]([CH3:16])[CH3:1])=[CH:4][C:5]=1[N+:13]([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 962Water2×HCID 14797Potassium HydroxideHCID 4396139N-[4-(dimethylamino)-2-nitrophenyl]acetamide

Product 1

HCID 27334524-Amino-N,N-dimethyl-3-nitroanilineYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-[4-(dimethylamino)-2-nitrophenyl]acetamide obtained in step 11 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 N-(4-amino-3-nitrophenyl)-N,N-dimethylamine. (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-c540b97dd5a64963ac6b323b56dcc6c9
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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