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

HRID 636716노트

반응식

HRID 636716 반응식
[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]

참가 물질

3

반응물 1

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-539bf8e21bb748a887149b5da52701f0
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06194454B1

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