Sodium Hydroxide → 4-Cyclopentylbenzene-1,2-diamine

HRID 1424223노트

반응식

HRID 1424223 반응식
[CH:1]1([C:6]2[CH:11]=[CH:10][C:9]([NH:12]C(=O)C)=[C:8]([N+:16]([O-])=O)[CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>[Pd]>[CH:1]1([C:6]2[CH:7]=[C:8]([NH2:16])[C:9]([NH2:12])=[CH:10][CH:11]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 86699135N-(4-cyclopentyl-2-nitrophenyl)acetamide

생성물 1

HCID 866990854-Cyclopentylbenzene-1,2-diamine수율 50%

시약·촉매·용매 1

HCID 23938Palladium촉매

반응 조건

온도
90 °C

실험 절차

A suspension of N-(4-cyclopentyl-2-nitrophenyl)acetamide (Preparation 86, 19.48 g, 78.46 mmol) in aqueous sodium hydroxide (6.0M, 100 mL, 600 mmol) was heated at 90° C. for 4 days. The reaction was allowed to cool and extracted with methylene chloride (3×). The organic layers were combined, dried over anhydrous magnesium sulphate, filtered, and concentrated in vacuo. The resulting residue was suspended in methanol (300 mL) and treated with palladium (2 g, 20 mmol, 10% on carbon, Degussa type). The reaction mixture was hydrogenated at 40 psi for 5 hours before filtering through celite and concentrating in vacuo. The residue was purified using silica gel column chromatography eluting with a 0-100% ethyl acetate/hexanes gradient to afford the title compound (6.85 g, 50%) as a purple solid.

후처리

  1. temperatureto cool
  2. extractionextracted with methylene chloride (3×)
  3. dry with materialdried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. filtrationbefore filtering through celite
  7. concentrationconcentrating in vacuo
  8. customThe residue was purified
  9. washeluting with a 0-100% ethyl acetate/hexanes gradient

출처 및 근거

ORD 기록
ord-982a0095b5f6425aa2be6f3be4760afe
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927587B2

반응 노트

불러오는 중…