Water → 6-Nitro-o-anisidine

HRID 1655467Notes

Reaction equation

HRID 1655467 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].[C:12](=O)([O-])[O-].[K+].[K+].CI.O>CN(C=O)C>[CH3:12][O:11][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[NH2:1]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 41154952-Amino-3-Nitrophenol

Product 1

HCID 854916-Nitro-o-anisidineYield 82.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-amino-3-nitrophenol (7.7 g) and potassium carbonate (7.6 g) in DMF (15 ml) was stirred for 30 minutes at room temperature and there was then added methyl iodide (7.8 g). The mixture was stirred for 5 further hours at room temperature. To the reaction mixture was added water, which was extracted with ethyl acetate. The organic layer was washed with water and, then, dried. The solvent was distilled off to give crude crystals and recrystallization from isopropyl ether gave orange prisms (6.9 g, 82%), m.p. 76-77° C.

Workup

  1. stirringThe mixture was stirred for 5 further hours at room temperature
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. customdried
  5. distillationThe solvent was distilled off
  6. customto give crude
  7. customcrystals and recrystallization from isopropyl ether

Sources & evidence

ORD record
ord-8d86b5be562048d882e4a2c67f3ce967
Source dataset
uspto-grants-1993_10
Patent number
US05250554

Reaction notes

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