Acetic Acid → 5,6,9,10-tetrahydro-4H-pyrido[3,2,1-jk]carbazol-11(8H)-one

HRID 1793571노트

반응식

HRID 1793571 반응식
Cl.[N:2]1(N=C2CCCC(O)=C2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1.Cl.[CH3:21][C:22]([OH:24])=O>>[CH:9]1[CH:8]=[CH:7][C:6]2[CH2:5][CH2:4][CH2:3][N:2]3[C:11]=2[C:10]=1[C:3]1[C:22](=[O:24])[CH2:21][CH2:6][CH2:5][C:4]=13

참가 물질

4

반응물 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 178479633HCID 178479633, 화합물

생성물 1

HCID 12347665,6,9,10-tetrahydro-4H-pyrido[3,2,1-jk]carbazol-11(8H)-one수율 33%

실험 절차

3-(3,4-Dihydro-1-(2H)-quinolinylimino)-1-cyclohexen-1-ol hydrochloride (4.78 g, 17 mmol) was mixed with AcOH (37 mL) and conc. HCl (6.1 mL). The reaction mixture was refluxed for 1 h and cooled to RT. The reaction mixture was concentrated in vacuo then the residue was dissolved in CH2Cl2. The organic solution was washed with H2O and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was chromatographed in silica gel (hex:EtOAc 1:1) to give 5,6,9,10-tetrahydro-4H-pyrido[3,2,1-jk]carbazol-11(8H)-one (1.25 g, 33%) as a light yellow solid.

후처리

  1. temperatureThe reaction mixture was refluxed for 1 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe residue was dissolved in CH2Cl2
  4. washThe organic solution was washed with H2O and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed in silica gel (hex:EtOAc 1:1)

출처 및 근거

ORD 기록
ord-427f376eea2545d9bee460fe1511bd36
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07081455B2

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