Water → 1-(5,5-Dimethyl-8-nitro-2,3,4,5-tetrahydrobenzo[b]azepin-1-yl)ethanone

HRID 423876노트

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HRID 423876 반응식
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][C:6]1([CH3:20])[CH2:12][CH2:11][CH2:10][NH:9][C:8]2[CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=[CH:16][C:7]1=2.C([O-])(O)=O.[Na+].O>C(Cl)Cl>[CH3:5][C:6]1([CH3:20])[CH2:12][CH2:11][CH2:10][N:9]([C:1](=[O:3])[CH3:2])[C:8]2[CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=[CH:16][C:7]1=2

참가 물질

6

반응물 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 574702565,5-dimethyl-8-nitro-2,3,4,5-tetrahydro-1H-benzo[b]azepine

생성물 1

HCID 578647131-(5,5-Dimethyl-8-nitro-2,3,4,5-tetrahydrobenzo[b]azepin-1-yl)ethanone수율 73.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Acetyl chloride (0.77 mL, 11 mmol) was added to a suspension of crude 5,5-dimethyl-8-nitro-2,3,4,5-tetrahydro-1H-benzo[b]azepine (1.2 g, 5.45 mmol) and NaHCO3 (1.37 g, 16.3 mmol) in CH2Cl2 (20 mL). The mixture was heated at reflux for 1 h. After cooling, the mixture was poured into water and extracted with CH2Cl2. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by column chromatography to afford 1-(5,5-dimethyl-8-nitro-2,3,4,5-tetrahydrobenzo[b]azepin-1-yl)ethanone (1.05 g, 64% over two steps).

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 h
  3. temperatureAfter cooling
  4. extractionextracted with CH2Cl2
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-1d3a4fbf394d4e89b17ce8bc8a3df196
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101767B2

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