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

HRID 1793571ノート

反応式

HRID 1793571 の反応式
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

参加物

4

反応物 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 178479633HCID 178479633、化合物

生成物 1

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

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-427f376eea2545d9bee460fe1511bd36
出典データセット
uspto-grants-2006_07
特許番号
US07081455B2

反応ノート

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