5-Chloroquinoline → 5-Chloro-1,2,3,4-tetrahydroquinoline

HRID 910059Notes

Reaction equation

HRID 910059 reaction equation
[Cl: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>C(O)(=O)C.C(OCC)C.[Pt]=O>[Cl: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

5

Reactant 1

HCID 694585-Chloroquinoline

Product 1

HCID 114806665-Chloro-1,2,3,4-tetrahydroquinolineYield 69%

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 5-chloroquinoline (10.0 g) and platinum oxide (50 mg) in acetic acid was shaken under a hydrogen atmosphere at room temperature for 4 hours. The mixture was diluted with diethyl ether and filtered through Celite. The volatiles were removed under reduced pressure and the residue was partitioned between saturated aqueous sodium bicarbonate and ethyl acetate (3×300 mL). The organic extracts were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified over silica gel and the fractions containing product were combined and concentrated under reduced pressure to provide 7.0 g (69%) of the desired compound.

Workup

  1. filtrationfiltered through Celite
  2. customThe volatiles were removed under reduced pressure
  3. customthe residue was partitioned between saturated aqueous sodium bicarbonate and ethyl acetate (3×300 mL)
  4. dry with materialThe organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified over silica gel
  8. additionthe fractions containing product
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e0b1c73caaab41a9b5ed905300678cd7
Source dataset
uspto-grants-2011_09
Patent number
US08022065B2

Reaction notes

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