HCID 136390993, compound → HCID 67290580, compound

HRID 511834Notes

Reaction equation

HRID 511834 reaction equation
[F:1][C:2]([F:18])([F:17])[CH2:3][O:4][C:5]1[CH:6]=[N:7][C:8]2[C:9](=[N:15]O)[CH2:10][CH2:11][CH2:12][C:13]=2[CH:14]=1>[Pd].CO>[F:18][C:2]([F:1])([F:17])[CH2:3][O:4][C:5]1[CH:6]=[N:7][C:8]2[CH:9]([NH2:15])[CH2:10][CH2:11][CH2:12][C:13]=2[CH:14]=1

Participants

4

Reactant 1

HCID 136390993HCID 136390993, compound

Product 1

HCID 67290580HCID 67290580, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-(2,2,2-trifluoroethoxy)-6,7-dihydroquinolin-8(5H)-one oxime (167 mg) and 10% palladium on carbon (100 mg) in methanol (7 mL) was stirred at room temperature for 24 h under hydrogen atmosphere (4 atm). Then, the mixture was filtered through a pad of Celite, and the filtrate was concentrated in vacuo. The residue was purified by column chromatography on NH-gel eluting with hexane/ethyl acetate (1:1-0:1) to give 68 mg (43% yield) of the title compound as a pale brown oil:

Workup

  1. filtrationThen, the mixture was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by column chromatography on NH-gel
  4. washeluting with hexane/ethyl acetate (1:1-0:1)

Sources & evidence

ORD record
ord-d6a4b98c497e4c388f9c335a876245aa
Source dataset
uspto-grants-2015_08
Patent number
US09101616B2

Reaction notes

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