3-Hydrazinylbenzonitrile → 9-Chloro-8-methoxy-6,6-dimethyl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 2202442노트

반응식

HRID 2202442 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8]([CH3:15])([CH3:14])[C:7](=O)[CH2:6][CH2:5]2.[NH:17]([C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[C:22]#[N:23])N>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][C:9]2[C:8]([CH3:15])([CH3:14])[C:7]3[NH:17][C:19]4[C:26]([C:6]=3[CH2:5][C:4]=2[CH:3]=1)=[CH:25][CH:24]=[C:21]([C:22]#[N:23])[CH:20]=4

참가 물질

4

반응물 2

HCID 14881453-HydrazinylbenzonitrileHCID 668344076-Chloro-7-methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one

생성물 1

HCID 668345029-Chloro-8-methoxy-6,6-dimethyl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

반응 조건

온도
90 °C

실험 절차

6-Chloro-7-methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one (Compound I1-1, 4.45 g, 16.5 mmol) and 3-hydrazinobenzonitrile (2.63 g, 1.2 eq.) were dissolved in TFA (91 mL), and stirred at 90° C. for 3 hours. According to the concentration under reduced pressure, TFA was removed and the residues were added with saturated aqueous solution of NaHCO3, followed by extraction with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were added with ethyl acetate. After stirring at room temperature, the precipitated solid was separated by filtration. The filtrate was concentrated under reduced pressure to obtain the target compound as a mixture with 11-3 (red powder, 6.46 g).

후처리

  1. concentrationAccording to the concentration under reduced pressure, TFA
  2. customwas removed
  3. additionthe residues were added with saturated aqueous solution of NaHCO3
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. customThe drying agent was removed by filtration
  8. customthe residues obtained
  9. concentrationafter concentration under reduced pressure
  10. additionwere added with ethyl acetate
  11. stirringAfter stirring at room temperature
  12. customthe precipitated solid was separated by filtration
  13. concentrationThe filtrate was concentrated under reduced pressure
  14. customto obtain the target compound as a mixture with 11-3 (red powder, 6.46 g)

출처 및 근거

ORD 기록
ord-5f67bce1097b464eb4f6b7b159bcbb7b
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365514B2

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