2,3-dihydro-1H-cyclopenta[b]quinoline → HCID 86606386, compound

HRID 1789668Notes

Reaction equation

HRID 1789668 reaction equation
[CH2:1]1[C:13]2[C:4](=[N:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[CH:12]=2)[CH2:3][CH2:2]1.[H][H]>CO.O=[Pt]=O>[CH2:1]1[C@@H:13]2[C@H:4]([NH:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[CH2:12]2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 3152112,3-dihydro-1H-cyclopenta[b]quinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 86606386HCID 86606386, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

The title compound was prepared by catalytic hydrogenation of 2,3-dihydro-1H-cyclopenta[b]quinoline (0.5 g, 2.43 mmol) in the presence of PtO2 and hydrogen (45 psi) in methanol (50 ml) to give the cis and trans isomers. Separation by flash chromatography (10–30% ethyl acetate/petroleum ether) gave the title compounds as light yellow solids (75%).

Workup

  1. customto give the cis and trans isomers
  2. customSeparation by flash chromatography (10–30% ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-47bf0c68953640b1a2190ebcddf47f03
Source dataset
uspto-grants-2006_07
Patent number
US07071185B2

Reaction notes

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