1,2-Dihydro-6-fluoro-5-hydroxymethylquinaldine → 6-Fluoro-5-hydroxymethyl-1,2,3,4-tetrahydroquinaldine

HRID 2418219Notes

Reaction equation

HRID 2418219 reaction equation
[F:1][C:2]1[C:3]([CH2:13][OH:14])=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([CH3:12])[CH:6]=[CH:5]2>C(O)C.Cl.[Pd].[Pt]>[F:1][C:2]1[C:3]([CH2:13][OH:14])=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([CH3:12])[CH2:6][CH2:5]2

Participants

6

Reactant 1

HCID 136692451,2-Dihydro-6-fluoro-5-hydroxymethylquinaldine

Product 1

HCID 544877736-Fluoro-5-hydroxymethyl-1,2,3,4-tetrahydroquinaldine

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 23939PlatinumCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A solid which was chiefly 1,2-dihydro-6-fluoro-5-hydroxymethylquinaldine (7.0 g) was dissolved in 200 ml of ethanol containing 1 ml of concentrated hydrochloric acid, 1.0 g of 5% palladium on charcoal, and 1.0 g 5% platinum on charcoal and the mixture was hydrogenated at 50 psi at 20° C. for 5 hours. The solution was filtered and the filtrate was evaporated to provide white solid 6-fluoro-5-hydroxymethyl-1,2,3,4-tetrahydroquinaldine as determined by nuclear magnetic resonance spectral analysis.

Workup

  1. filtrationThe solution was filtered
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-ab5319c31ff2467e9fd4335e71cfea98
Source dataset
uspto-grants-1984_09
Patent number
US04472405

Reaction notes

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