Aluminium lithium hydride → 5-Ethyl-5,6-dihydro-phenanthridin-9-ylamine

HRID 968283ノート

反応式

HRID 968283 の反応式
[CH2:1]([N:3]1[C:16](=O)[C:15]2[C:10](=[CH:11][C:12]([N+:18]([O-])=O)=[CH:13][CH:14]=2)[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]1=2)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:1]([N:3]1[CH2:16][C:15]2[C:10](=[CH:11][C:12]([NH2:18])=[CH:13][CH:14]=2)[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]1=2)[CH3:2]

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 222885445-ethyl-9-nitro-5H-phenanthridin-6-one

生成物 1

HCID 222885425-Ethyl-5,6-dihydro-phenanthridin-9-ylamine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
23 °C

実験手順

A solution of 5-ethyl-9-nitro-5H-phenanthridin-6-one I-1d (250 mg, 0.93 mmol) in THF (1 ml) was added to a suspension of lithium aluminum hydride (99 mg, 2.6 mmol) in THF (5 ml). The reaction mixture was heated to reflux for 2 h and cooled to 23° C. Excess hydride was quenched by careful sequential addition of water (5 drops from a Pasteur pipet), 1N aqueous sodium hydroxide (5 drops from a Pasteur pipet), and water (15 drops from a Pasteur pipet). Insolubles were removed by filtration, and the filter cake was washed with ethyl acetate (2 5-ml portions). The combined filtrates were washed with water (10 ml) and saturated aqueous sodium chloride (10 ml). The organics were dried over anhydrous sodium sulfate and were concentrated. The residue was purified by flash column chromatography (2% ethyl acetate in dichloromethane) to provide 5-ethyl-5,6-dihydro-phenanthridin-9-ylamine I-13a (52 mg, 25%).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 h
  3. customExcess hydride was quenched by careful sequential addition of water (5 drops from a Pasteur pipet), 1N aqueous sodium hydroxide (5 drops from a Pasteur pipet), and water (15 drops from a Pasteur pipet)
  4. customInsolubles were removed by filtration
  5. washthe filter cake was washed with ethyl acetate (2 5-ml portions)
  6. washThe combined filtrates were washed with water (10 ml) and saturated aqueous sodium chloride (10 ml)
  7. dry with materialThe organics were dried over anhydrous sodium sulfate
  8. concentrationwere concentrated
  9. customThe residue was purified by flash column chromatography (2% ethyl acetate in dichloromethane)

出典と根拠

ORDレコード
ord-80bfc75e312544be8bff9bf79c544a4f
出典データセット
uspto-grants-2005_10
特許番号
US06958347B2

反応ノート

読み込み中…