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

HRID 327472

Reaktionsgleichung

Reaktionsgleichung von HRID 327472
[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]

Komponenten

5

Edukt 2

HCID 792913-Methyl-2-nitroanisoleHCID 178418361HCID 178418361, Verbindung2×

Produkt 1

HCID 4592492-Methoxy-6-methylanilineAusbeute 100,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-451fa53053664fa6bc4947e3129370d4
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05273975

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