Triethylamine → 7-(Trifluoromethyl)quinoline

HRID 657768Notes

Reaction equation

HRID 657768 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.C(N(CC)CC)C>[Pd].CO>[F:15][C:12]([F:13])([F:14])[C:8]1[CH:7]=[C:6]2[C:11]([CH:2]=[CH:3][CH:4]=[N:5]2)=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 676684-Chloro-7-(trifluoromethyl)quinoline

Product 1

HCID 4596147-(Trifluoromethyl)quinoline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-Chloro-7-(trifluoromethyl)quinoline (9.35 g, 0.0404 mol) was hydrogenated in the presence of 5% palladium on carbon (4 g) in methanol (180 mL) in the presence of triethylamine (6 mL). The solution was stirred for 3.5 hours, and then filtered through Celite. The filtrate was concentrated under reduced pressure, and the residue was treated with ethyl acetate and water. The organic layer was separated, washed with water (2×75 mL), dried over MgSO4, filtered, and concentrated under reduced pressure to a yellow solid.

Workup

  1. filtrationfiltered through Celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. additionthe residue was treated with ethyl acetate and water
  4. customThe organic layer was separated
  5. washwashed with water (2×75 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure to a yellow solid

Sources & evidence

ORD record
ord-7e1175e3eff24a31a75d8f8b247a79c0
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Reaction notes

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