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

HRID 417813Notes

Reaction equation

HRID 417813 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+]>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

4

Reactant 2

HCID 742185-Chloro-2-nitroanilineHCID 10942334Sodium Methoxide

Product 1

HCID 853005-Methoxy-2-nitroanilineYield 93.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

10 g of 5-chloro-2-nitroaniline are dissolved in 100 ml of methanol, and 32.3 g of sodium methoxide are added. The reaction mixture is heated at the boil under reflux for 18 hours. After cooling, the mixture is evaporated to dryness, 500 ml of water are added, and the crude product is isolated by filtration. Drying gives 9.15 g of 5-methoxy-2-nitroaniline.

Workup

  1. temperatureThe reaction mixture is heated at the boil
  2. temperatureunder reflux for 18 hours
  3. temperatureAfter cooling
  4. customthe mixture is evaporated to dryness, 500 ml of water
  5. additionare added
  6. customthe crude product is isolated by filtration
  7. customDrying

Sources & evidence

ORD record
ord-e21e12bcfccb420281768b7ca8abdaf5
Source dataset
uspto-grants-2012_01
Patent number
US08093240B2

Reaction notes

Loading…