5-Bromo-6-fluoro-2-methylquinoline → 5-Bromo-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline

HRID 1589257Notes

Reaction equation

HRID 1589257 reaction equation
[Br:1][C:2]1[C:11]([F:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:13])=[N:7]2.[H][H]>C(O)(=O)C.[Pt]>[Br:1][C:2]1[C:11]([F:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH:6]([CH3:13])[NH:7]2

Participants

5

Reactant 2

HCID 130353135-Bromo-6-fluoro-2-methylquinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 128968175-Bromo-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 20 g of 5-bromo-6-fluoroquinaldine in 150 ml of glacial acetic acid was added 2.0 g of platinum on charcoal. The mixture was hydrogenated on a Paar apparatus at a temperature of about 20° C. until the theoretical amount of hydrogen was taken up. The mixture was then filtered through celite to provide a solution of 5-bromo-6-fluoro-1,2,3,4-tetrahydroquinaldine. Evaporation of the solvent provides the desired intermediate. This intermediate could be used directly in Part C below without purification.

Workup

  1. filtrationThe mixture was then filtered through celite

Sources & evidence

ORD record
ord-e5af20ace377474ba08881a5e0eb9366
Source dataset
uspto-grants-1986_02
Patent number
US04568750

Reaction notes

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