2-Nitropropane → 3-(2-Methyl-2-nitropropyl)-7-(benzyloxy)indole

HRID 8088

反応式

HRID 8088 の反応式
CN([CH2:4][C:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[C:13]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:8]=2[NH:7][CH:6]=1)C.[OH-].[Na+].[N+:24]([CH:27]([CH3:29])[CH3:28])([O-:26])=[O:25]>CCOCC>[CH3:28][C:27]([N+:24]([O-:26])=[O:25])([CH3:29])[CH2:4][C:5]1[C:9]2[C:8](=[C:13]([O:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:12]=[CH:11][CH:10]=2)[NH:7][CH:6]=1

参加物

5

反応物 3

HCID 3982-Nitropropane2 回HCID 14798Sodium HydroxideHCID 2608077-Benzyloxygramine

生成物 1

HCID 220147783-(2-Methyl-2-nitropropyl)-7-(benzyloxy)indole収率 92.1%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

A mixture of 7-benzyloxy gramine (1.99 g, 7.10 mmol), solid NaOH (298 mg, 7.22 mmol) and 2-nitropropane (4.5 mL, 50 mmol) is heated to reflux. After 10 minutes at reflux, a thick slurry developed which is difficult to stir. Gas evolution is observed, and an additional 1 mL of 2-nitropropane is added to loosen the mixture. After 29 hours, the mixture is allowed to cool to ambient temperature. Ether (30 mL) is added and the mixture is filtered. The filtrate is treated with 10% acetic acid (6 mL), the layers are separated and the organic layer is rinsed with water (2×25 mL). The organic layer is dried (Na2SO4) and concentrated to give 2.12 g of 3-(2-methyl-2-nitropropyl)-7-(benzyloxy)indole (92%). MS (ES+) m/z 325.

後処理

  1. temperatureis heated to reflux
  2. temperatureAfter 10 minutes at reflux
  3. filtrationthe mixture is filtered
  4. additionThe filtrate is treated with 10% acetic acid (6 mL)
  5. customthe layers are separated
  6. washthe organic layer is rinsed with water (2×25 mL)
  7. dry with materialThe organic layer is dried (Na2SO4)
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-e4c5726ac3974685a58e1ea2a6c0c8f7
出典データセット
uspto-grants-2006_08
特許番号
US07087635B2

関連ノート

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