5-Chloro-2-nitroaniline → 5-Methoxy-2-nitroaniline

HRID 1061127Notes

Reaction equation

HRID 1061127 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].[CH3:12][O-:13].[Na+]>CN(C)C=O.CO>[CH3:12][O:13][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7]

Participants

5

Reactant 2

HCID 742185-Chloro-2-nitroanilineHCID 10942334Sodium Methoxide

Product 1

HCID 853005-Methoxy-2-nitroanilineYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-chloro-2-nitroaniline (5.0 g) in dimethylformamide (25 ml) was added 24% sodium methoxide in methanol (11 ml) and the mixture was heated at 80° C. for 4 hours. At the end of this time, the reaction mixture was cooled to room temperature and partitioned between ethyl acetate and water. The extract was washed with 20% aqueous sodium chloride solution and insoluble material was filtered off. The filtrate was concentrated in vacuo to give the desired compound (4.8 g, yield 99%).

Workup

  1. temperatureAt the end of this time, the reaction mixture was cooled to room temperature
  2. custompartitioned between ethyl acetate and water
  3. washThe extract was washed with 20% aqueous sodium chloride solution and insoluble material
  4. filtrationwas filtered off
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9e9bf923a03f4a33a97cb356cb3bc4ff
Source dataset
uspto-grants-2003_02
Patent number
US06525220B2

Reaction notes

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