Water → 6(5H)-Phenanthridinone

HRID 2090542

반응식

HRID 2090542 반응식
Br[C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5].C(=O)([O-])[O-].[Na+].[Na+].O>CC(N(C)C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:11]1[C:12]2[C:13]3[C:3](=[CH:2][CH:16]=[CH:15][CH:14]=3)[C:4](=[O:5])[NH:6][C:7]=2[CH:8]=[CH:9][CH:10]=1

참가 물질

6

반응물 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 25126Benzamide, 2-bromo-N-phenyl-

생성물 1

HCID 18536(5H)-Phenanthridinone수율 52%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 31374Dimethylacetamide용매

반응 조건

온도
160 °C

실험 절차

Then, in a nitrogen atmosphere, 2-bromo-N-phenylbenzamide (17.3 g, 62.7 mmol), palladium acetate (0.70 g, 3.1 mmol), and sodium carbonate (13.3 g, 125 mmol) were dissolved in dimethylacetamide (300 mL), followed by stirring and heating at 160° C. for 6 hours to cause reaction. The reaction solution was cooled to room temperature and then poured into cooled water, followed by extraction with ethyl acetate. The organic layer was dried with sodium sulfate, followed by filtration. The filtrate was concentrated using a rotary evaporator. The residue was collected by filtration and then successively washed with hexane and water. Thus, 6-phenanthridinone (6.36 g, 32.6 mmol) was obtained in a yield of 52%.

후처리

  1. customreaction
  2. temperatureThe reaction solution was cooled to room temperature
  3. additionpoured
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. filtrationfollowed by filtration
  7. concentrationThe filtrate was concentrated
  8. customa rotary evaporator
  9. filtrationThe residue was collected by filtration
  10. washsuccessively washed with hexane and water

출처 및 근거

ORD 기록
ord-270f6ea915b6400085148bc1cbd8360a
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08436173B2

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