2-Methoxy-4-nitroaniline → 2-Methoxy-4-nitrophenol

HRID 1085282Notes

Reaction equation

HRID 1085282 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH3:12].[OH-:13].[Na+]>O>[CH3:12][O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[OH:13]

Participants

4

Reactant 2

HCID 73372-Methoxy-4-nitroanilineHCID 14798Sodium Hydroxide

Product 1

HCID 767382-Methoxy-4-nitrophenolYield 8.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

50 g of 2-amino-5-nitroanisole, 50 g of sodium hydroxide were dissolved in 450 ml of water. The resultant mixture was heated under reflux for 3 hours and then ice-cooled. Precipicated crystals were collected by filtration, followed by dissolution in water. The thus-prepared solution was neutralized with 6 N hydrochloric acid and crystals thus precipitated were collected by filtration. The crystals were dissolved in chloroform. The resultant solution was washed with water and dried over anhydrous sodium sulfate. By concentrating the chloroform layer under reduced pressure, 4.5 g of 2-methoxy-4-nitrophenol were obtained as crystals.

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureice-cooled
  3. filtrationwere collected by filtration
  4. dissolutionfollowed by dissolution in water
  5. customthus precipitated
  6. filtrationwere collected by filtration
  7. dissolutionThe crystals were dissolved in chloroform
  8. washThe resultant solution was washed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationBy concentrating the chloroform layer under reduced pressure

Sources & evidence

ORD record
ord-c342fa1c7bc2472185eb740198f82fd4
Source dataset
uspto-grants-1991_04
Patent number
US05008267

Reaction notes

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