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

HRID 1424223ノート

反応式

HRID 1424223 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 866990854-Cyclopentylbenzene-1,2-diamine収率 50%

試薬・触媒・溶媒 1

HCID 23938Palladium触媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-982a0095b5f6425aa2be6f3be4760afe
出典データセット
uspto-grants-2015_01
特許番号
US08927587B2

反応ノート

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