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

HRID 1272208

반응식

HRID 1272208 반응식
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

참가 물질

5

반응물 3

HCID 3982-Nitropropane2회HCID 14798Sodium HydroxideHCID 2608077-Benzyloxygramine

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-49a35df9e60d4d9fabde5fc1b0560cc3
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07208505B2

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