Methyl iodide → 6-Nitro-o-anisidine

HRID 651381Notes

Reaction equation

HRID 651381 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].[OH-].[K+].[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 14797Potassium HydroxideHCID 41154952-Amino-3-Nitrophenol

Product 1

HCID 854916-Nitro-o-anisidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-hydroxy-6-nitroaniline (41 g; 0.266 mol) and 85% KOH (17.5 g; 0.266 mol) in anhydrous DMF (80 ml), CH3I (16.5 ml; 0.266 mol) was added dropwise. The reaction mixture was stirred at room temperature for 4 hours then poured into ice-water, the title compound precipitated as a brown solid. 40 g; m.p. 67-68° C.

Workup

  1. additionwas added dropwise
  2. customthe title compound precipitated as a brown solid

Sources & evidence

ORD record
ord-633658a5e57a4c82a413cccbea51478f
Source dataset
uspto-grants-2001_08
Patent number
US06281218B1

Reaction notes

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