5-Fluoroquinoline → 5-Fluoro-1,2,3,4-tetrahydroquinoline

HRID 1520170Notes

Reaction equation

HRID 1520170 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2>[Pd].CO>[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][NH:7]2

Participants

4

Reactant 1

HCID 1152435-Fluoroquinoline

Product 1

HCID 162443815-Fluoro-1,2,3,4-tetrahydroquinolineYield 70.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium on carbon (10%, 1.25 g) was added to a solution of 5-fluoroquinoline (2.5 g, 16.99 mmol) in methanol and the reaction was overnight at room temperature under an atmosphere of hydrogen. The reaction mixture was filtered through Celite and concentrated in vacuo to afford 5-fluoro-1,2,3,4-tetrahydroquinoline as a colorless oil (1.80 g, 70%).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-55d96f829f2b453fb48b82bbbfc19a3a
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

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