Hydrochloric Acid → 3-Methoxy-2-methyl-6-nitroaniline

HRID 327449Notes

Reaction equation

HRID 327449 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[C:6]([CH3:15])=[C:7]([NH2:14])[C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=1.Cl>CO>[CH3:1][O:2][C:5]1[C:6]([CH3:15])=[C:7]([NH2:14])[C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 129530203-Chloro-2-methyl-6-nitroaniline

Product 1

HCID 3501803-Methoxy-2-methyl-6-nitroanilineYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Sodium methoxide in methanol (110 mL of 25% solution, 0.49 mol, 20 equiv) was added to a stirred suspension of 3-chloro-2-methyl-6-nitrobenzenamine (4.0 g, 23.5 mmol) in methanol (250 mL) and the mixture was stirred at reflux for 18 hours. The solution was cooled, neutralized with methanolic hydrogen chloride, filtered to remove sodium chloride, and the solvent was removed under reduced pressure. The residual solid was partitioned between ethyl acetate and water. Evaporation of the ethyl acetate gave 3.7 g (86%) of 3-methoxy-2-methyl-6-nitrobenzenamine.

Workup

  1. temperatureat reflux for 18 hours
  2. temperatureThe solution was cooled
  3. filtrationfiltered
  4. customto remove sodium chloride
  5. customthe solvent was removed under reduced pressure
  6. customThe residual solid was partitioned between ethyl acetate and water
  7. customEvaporation of the ethyl acetate

Sources & evidence

ORD record
ord-576c355e0ffe4e789dd5fa27c44fb867
Source dataset
uspto-grants-1993_12
Patent number
US05273975

Reaction notes

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