3-Methyl-2-nitroanisole → 2-Methoxy-6-methylaniline

HRID 327472Notes

Reaction equation

HRID 327472 reaction equation
[CH3:1][C:2]1[C:3]([N+:10]([O-])=O)=[C:4]([O:8][CH3:9])[CH:5]=[CH:6][CH:7]=1.[H][H]>C(O)C.[Pd]>[CH3:9][O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[NH2:10]

Participants

5

Reactant 2

HCID 792913-Methyl-2-nitroanisoleHCID 178418361HCID 178418361, compound2×

Product 1

HCID 4592492-Methoxy-6-methylanilineYield 100.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Palladium charcoal (1.0 g of 10%) was added to a solution of 3-methyl-2-nitroanisole (16.8 g, 0.1 mol) in ethanol (150 mL) and the solution was hydrogenated (50 lb initial hydrogen pressure) until hydrogen uptake ceased (2 hours). The solution was filtered and evaporated to give 13.8 g of 2-methoxy-6-methylbenzenamine (compound XLIV) as an oil. The product was dissolved in acetic anhydride (100 mL) and the resulting solution was refluxed for 1 hour. Part of the solvent (50 mL) was slowly removed over a 1-hour period, after which time the solution was cooled and the remainder of the solvent was removed under reduced pressure. The residual oil was crystallized from ethyl acetate:hexane (200 mL of 1:2) to give 20.5 g of N-acetyl-N-(2-methoxy-6-methylphenyl)-acetamide, mp 116°-119° C. Anal Calcd for C12H15NO3 : C, 65.14; H, 6.83; N, 6.33. Found: C, 65.44; H, 7.04; N, 6.39.

Workup

  1. custom(2 hours)
  2. filtrationThe solution was filtered
  3. customevaporated

Sources & evidence

ORD record
ord-451fa53053664fa6bc4947e3129370d4
Source dataset
uspto-grants-1993_12
Patent number
US05273975

Reaction notes

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