HCID 67290054, compound → HCID 67291901, compound

HRID 511829Notes

Reaction equation

HRID 511829 reaction equation
[F:1][C:2]([F:16])([F:15])[CH2:3][O:4][C:5]1[CH:6]=[N:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2>C(O)(C(F)(F)F)=O.[Pt](=O)=O>[F:16][C:2]([F:1])([F:15])[CH2:3][O:4][C:5]1[CH:6]=[N:7][C:8]2[CH2:9][CH2:10][CH2:11][CH2:12][C:13]=2[CH:14]=1

Participants

4

Reactant 1

HCID 67290054HCID 67290054, compound

Product 1

HCID 67291901HCID 67291901, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 3-(2,2,2-trifluoroethoxy)quinoline (1.13 g, 5.0 mmol) and platinum (IV) oxide (50 mg) in TFA (8 mL) was stirred at room temperature for 12 hours under hydrogen atmosphere (1 atm). Then the mixture was filtered off through a pad of Celite, and the filtrate was concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (10:1-7:1) to give 495 mg (43% yield) of the title compound as a colorless oil:

Workup

  1. filtrationThen the mixture was filtered off through a pad of Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (10:1-7:1)

Sources & evidence

ORD record
ord-d35bfd1eb24647a8bb41246145d7d090
Source dataset
uspto-grants-2015_08
Patent number
US09101616B2

Reaction notes

Loading…