1,2-Dihydro-6-fluoro-5-hydroxymethylquinaldine → 6-Fluoro-2,5-dimethyl-1,2,3,4-tetrahydroquinoline

HRID 1381277Notes

Reaction equation

HRID 1381277 reaction equation
[F:1][C:2]1[C:3]([CH2:13]O)=[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.[Pt].[Pd]>[F:1][C:2]1[C:3]([CH3:13])=[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 136692466-Fluoro-2,5-dimethyl-1,2,3,4-tetrahydroquinoline

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 23939PlatinumCatalyst2×HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent2×

Procedure

A solid which was chiefly 1,2-dihydro-6-fluoro-5-hydroxymethylquinaldine (13.2 g) prepared according to Example 2 was dissolved in 300 ml of ethanol and 10 ml of concentrated hydrochloric acid. To this solution was added 1 g of 5% platinum on charcoal and 3 g of 5% palladium on charcoal. The solution was hydrogenated at 50 psi at about 20° C. on a Paar apparatus. After absorption of about 12 psi of hydrogen (the theoretical amount needed), the solution was filtered and the solvent was removed by evaporation to provide a solid. Nuclear magnetic resonance spectral analysis showed slightly incomplete reduction. Therefore the solid was dissolved in 300 ml of aqueous (95%) ethanol to which 2 g of platinum on charcoal was added, and the solution was hydrogenated at 50 psi on the Paar apparatus for about 16 hours. The solution was then filtered and the solvent was evaporated. The solid recovered was dissolved in 50 ml of water. This solution was basified with aqueous sodium hydroxide and then extracted with diethyl ether. Evaporation of the ether provided 6-fluoro-5-methyl-1,2,3,4-tetrahydroquinaldine as an oil.

Workup

  1. customprepared
  2. customwas hydrogenated at 50 psi at about 20° C. on a Paar apparatus
  3. customAfter absorption of about 12 psi of hydrogen (the theoretical amount
  4. filtrationwas filtered
  5. customthe solvent was removed by evaporation
  6. customto provide a solid
  7. additionwas added
  8. filtrationThe solution was then filtered
  9. customthe solvent was evaporated
  10. customThe solid recovered
  11. dissolutionwas dissolved in 50 ml of water
  12. extractionextracted with diethyl ether
  13. customEvaporation of the ether

Sources & evidence

ORD record
ord-e251befcc9b84aec9b6b215c260a3330
Source dataset
uspto-grants-1986_04
Patent number
US04585868

Reaction notes

Loading…