Tetrahydrofuran → 2'-Hydroxy-4'-methoxyacetanilide

HRID 270057

反応式

HRID 270057 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[OH:12])([O-])=O.[H][H].C1C[O:18][CH2:17][CH2:16]1>[Pd]>[OH:12][C:5]1[CH:6]=[C:7]([O:10][CH3:11])[CH:8]=[CH:9][C:4]=1[NH:1][C:17](=[O:18])[CH3:16]

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 2196355-Methoxy-2-nitrophenolHCID 178418361HCID 178418361、化合物

生成物 1

HCID 41051392'-Hydroxy-4'-methoxyacetanilide収率 80%

試薬・触媒・溶媒 1

HCID 23938Palladium触媒

反応条件

温度
60 °C

実験手順

2-Nitro-5-methoxyphenol (prepared from 3-methoxyphenol, R. J. Maleski, Synthetic Communications, 1993, 23, 343-348) (48.5 g, 0.287 mol) dissolved in THF (1.5 L) was hydrogenated at ambient temperature over night with 10% palladium on carbon (10 g) until 20.3 L of hydrogen was consumed. After filtration and evaporation the residue was suspended in degased water (1.7 L) and acetic anhydride (42.5 mL) was added with stirring. The mixture was heated to 60° C. for 1 h and then cooled to room temperature. The volatiles were removed in vacuo and the solid was washed thoroughly with water and dried in vacuo to give brick-red crystals (41.7 g, 80%).

後処理

  1. customwas consumed
  2. filtrationAfter filtration and evaporation the residue
  3. additionacetic anhydride (42.5 mL) was added
  4. temperaturecooled to room temperature
  5. customThe volatiles were removed in vacuo
  6. washthe solid was washed thoroughly with water
  7. customdried in vacuo

出典と根拠

ORDレコード
ord-9dc2eff7eedb4014bf7a9f83c185b290
出典データセット
uspto-grants-2008_11
特許番号
US07449475B2

関連ノート

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