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

HRID 727796Notes

Reaction equation

HRID 727796 reaction equation
[N:1]1([C:11]2[CH2:16][CH2:15][CH2:14][C:13](=[O:17])[CH:12]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.O>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:8]1[CH:7]=[CH:6][C:5]2[CH2:4][CH2:3][CH2:2][N:1]3[C:10]=2[C:9]=1[C:12]1[C:13](=[O:17])[CH2:14][CH2:15][CH2:16][C:11]=13

Participants

5

Reactant 2

HCID 962WaterHCID 198250893-(1,2,3,4-Tetrahydro-1-quinolinyl)-2-cyclohexen-1-one

Product 1

HCID 12347665,6,9,10-tetrahydro-4H-pyrido[3,2,1-jk]carbazol-11(8H)-oneYield 98.9%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

Cupric acetate (878 mg) was added to a solution of 3-(1,2,3,4-tetrahydro-1-quinolinyl)-2-cyclohexen-1-one (500 mg) and palladium (II) acetate (100 mg) in dry DMF (10 ml). The mixture was heated at 135° under nitrogen for 3 h, cooled, poured into water (100 ml) and extracted with ethyl acetate (4×50 ml). The combined, dried organic extracts were evaporated to give a solid (ca. 490 mg) which was purified by FCC eluting with ethyl acetate:hexane (2:1) to give the title compound (285 mg), m.p. 160°-164°.

Workup

  1. temperatureThe mixture was heated at 135° under nitrogen for 3 h
  2. temperaturecooled
  3. extractionextracted with ethyl acetate (4×50 ml)
  4. customdried organic extracts were evaporated

Sources & evidence

ORD record
ord-290480eea39c42768e2d2e301450b9c5
Source dataset
uspto-grants-1991_09
Patent number
US05045545

Reaction notes

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