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

HRID 327472

反応式

HRID 327472 の反応式
[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]

参加物

5

反応物 2

HCID 792913-Methyl-2-nitroanisoleHCID 178418361HCID 178418361、化合物2 回

生成物 1

HCID 4592492-Methoxy-6-methylaniline収率 100.6%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-451fa53053664fa6bc4947e3129370d4
出典データセット
uspto-grants-1993_12
特許番号
US05273975

関連ノート

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