2,3-Dimethyl-4-nitroanisole → 4-Methoxy-2,3-dimethylaniline

HRID 1743395

Reaction equation

HRID 1743395 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[C:5]([CH3:12])[C:4]=1[CH3:13].[H][H]>C(O)C.[C].[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[C:5]([CH3:12])[C:4]=1[CH3:13]

Participants

5

Reactant 2

HCID 5964652,3-Dimethyl-4-nitroanisoleHCID 178418361HCID 178418361, compound

Product 1

HCID 110948094-Methoxy-2,3-dimethylanilineYield 70%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

4-Methoxy-2,3-dimethylnitrobenzene (21.1 g, 0.15 mol) was dissolved in ethanol (300 mL), and 10% palladium carbon (50% hydrate, 1.36 g) was added. The mixture was reacted at 40° C. for 2 hours under the hydrogen atmosphere. After cooling, the catalyst was removed, ethanol was distilled off under reduced pressure, and the residue was diluted with ethyl acetate. The dilution was washed with 5% sodium hydrosulfite, dried over sodium sulfate, and purified by small amount silica gel column chromatography (ethyl acetate, 1:1). The solvent was distilled off under reduced pressure, followed by recrystallization from hexane, to obtain 15.8 g of the title compound.

Workup

  1. temperatureAfter cooling
  2. customthe catalyst was removed
  3. distillationethanol was distilled off under reduced pressure
  4. additionthe residue was diluted with ethyl acetate
  5. washThe dilution was washed with 5% sodium hydrosulfite
  6. dry with materialdried over sodium sulfate
  7. custompurified by small amount silica gel column chromatography (ethyl acetate, 1:1)
  8. distillationThe solvent was distilled off under reduced pressure
  9. customfollowed by recrystallization from hexane

Sources & evidence

ORD record
ord-41a00319aad84bef96212bf30c6ab15a
Source dataset
uspto-grants-2006_03
Patent number
US07008940B1

Linked notes

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