Methyl iodide → 6-Nitro-o-anisidine

HRID 1661898Notes

Reaction equation

HRID 1661898 reaction equation
[OH:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[C:3]=1[NH2:4].[H-].[Na+].[CH3:14]I>CN(C=O)C>[CH3:14][O:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[C:3]=1[NH2:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 41154952-Amino-3-Nitrophenol

Product 1

HCID 854916-Nitro-o-anisidineYield 91.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 20 g (129.9 mmol) 2-hydroxy-6-nitroaniline in 150 ml DMF, NaH (3.42 g, 143 mmol, 95%) is added at 0° C. and stirring is continued for 1.5 h. MeI (9.3 ml, 150 mmol) is added and the reaction mixture is stirred at room temperature for 1 h. After that the reaction mixture is poured on water and extracted (3×) with ethyl acetate. The combined organic layers are washed with water (2×) and brine, dried over MgSO4, filtered and concentrated in vacuo. To the residue 50 ml of hexane:diethyl ether=4:1 is added and the resulting suspension is stirred for 5 minutes. 20 g of the title compound are obtained after filtration of the mixture as a brown crystalline solid.

Workup

  1. stirringthe reaction mixture is stirred at room temperature for 1 h
  2. additionAfter that the reaction mixture is poured on water
  3. extractionextracted (3×) with ethyl acetate
  4. washThe combined organic layers are washed with water (2×) and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. additionTo the residue 50 ml of hexane:diethyl ether=4:1 is added
  9. stirringthe resulting suspension is stirred for 5 minutes

Sources & evidence

ORD record
ord-3d04793ea85c4b639d3049f3740c7cad
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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