2-(3-Isopropyl-4-hydroxy-phenoxy)-3-methyl-5-nitrobenzonitrile → 5-Amino-2-(3-isopropyl-4-hydroxy-phenoxy)-3-methyl-benzonitrile

HRID 636716ノート

反応式

HRID 636716 の反応式
[CH:1]([C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][C:22]=1[OH:23])[O:7][C:8]1[C:15]([CH3:16])=[CH:14][C:13]([N+:17]([O-])=O)=[CH:12][C:9]=1[C:10]#[N:11])([CH3:3])[CH3:2]>C(O)C>[NH2:17][C:13]1[CH:14]=[C:15]([CH3:16])[C:8]([O:7][C:6]2[CH:20]=[CH:21][C:22]([OH:23])=[C:4]([CH:1]([CH3:2])[CH3:3])[CH:5]=2)=[C:9]([CH:12]=1)[C:10]#[N:11]

参加物

3

反応物 1

HCID 155236452-(3-Isopropyl-4-hydroxy-phenoxy)-3-methyl-5-nitrobenzonitrile

生成物 1

HCID 155236465-Amino-2-(3-isopropyl-4-hydroxy-phenoxy)-3-methyl-benzonitrile収率 77.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of 2-(3-isopropyl-4-hydroxy-phenoxy)-3-methyl-5-nitrobenzonitrile (215 mg) and stannous chloride (776 mg) in ethanol (5 mL) was refluxed for 2 h, cooled, quenched with saturated aqueous sodium bicarbonate and concentrated in vacuo. The residue was extracted with ethyl acetate, the organics washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was flash chromatographed (40% ethyl acetate/hexanes) to afford 5-amino-2-(3-isopropyl-4-hydroxy-phenoxy)-3-methyl-benzonitrile as a colorless foam (150 mg).

後処理

  1. temperaturecooled
  2. customquenched with saturated aqueous sodium bicarbonate
  3. concentrationconcentrated in vacuo
  4. extractionThe residue was extracted with ethyl acetate
  5. washthe organics washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customchromatographed (40% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-539bf8e21bb748a887149b5da52701f0
出典データセット
uspto-grants-2001_02
特許番号
US06194454B1

反応ノート

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