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Water → 8-cyano-3,4-dihydro-1H-1-benzazepine-2,5-dione

HRID 1672190
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HRID 1672190 반응식
I[C:2]1[CH:14]=[CH:13][C:5]2[C:6](=[O:12])[CH2:7][CH2:8][C:9](=[O:11])[NH:10][C:4]=2[CH:3]=1.CCOC(C)=O.O.[CH3:22][N:23](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:22]([C:2]1[CH:14]=[CH:13][C:5]2[C:6](=[O:12])[CH2:7][CH2:8][C:9](=[O:11])[NH:10][C:4]=2[CH:3]=1)#[N:23]
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7

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HCID 962WaterHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 584766238-iodo-2,3,4,5-tetrahydro-1H-1-benzazepine-2,5-dione

생성물 1

HCID 673375958-cyano-3,4-dihydro-1H-1-benzazepine-2,5-dione수율 70%

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)
촉매
HCID 178418397HCID 178418397, 화합물촉매

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온도
80 °C

실험 절차

To a solution of 8-iodo-3,4-dihydro-1H-1-benzazepine-2,5-dione (0.3 g, 1.0 mmol) in DMF (5 mL) was added Zn(CN)2 (0.12 g, 1.0 mmol) and Pd(PPh3)4 (116 mg, 0.1 mmol). The reaction mixture was allowed to stir at 80° C. for 3.5 h. After being allowed to cool to rt, EtOAc (20 mL) and H2O (20 mL) were added, the organic solution was separated, and the aqueous solution was extracted with EtOAc (2×50 mL). The organic solutions were combined, washed with H2O and brine, dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography to provide 8-cyano-3,4-dihydro-1H-1-benzazepine-2,5-dione (140 mg, 70%).

후처리

  1. temperatureto cool to rt
  2. customthe organic solution was separated
  3. extractionthe aqueous solution was extracted with EtOAc (2×50 mL)
  4. washwashed with H2O and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-071fd125cd06410382ba660cd801c44a
출처 데이터셋
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07998952B2

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