3-(benzyloxy)-2-methyl-1-(2,2,2-trifluoroethyl)pyridin-4(1H)-one → 3-hydroxy-2-methyl-1-(2,2,2-trifluoroethyl)pyridin-4(1H)-one

HRID 1519027Notes

Reaction equation

HRID 1519027 reaction equation
C([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([CH2:16][C:17]([F:20])([F:19])[F:18])[C:10]=1[CH3:21])C1C=CC=CC=1>[Pd].CO>[OH:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([CH2:16][C:17]([F:20])([F:18])[F:19])[C:10]=1[CH3:21]

Participants

4

Reactant 1

HCID 708052203-(benzyloxy)-2-methyl-1-(2,2,2-trifluoroethyl)pyridin-4(1H)-one

Product 1

HCID 498698813-hydroxy-2-methyl-1-(2,2,2-trifluoroethyl)pyridin-4(1H)-oneYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-(Benzyloxy)-2-methyl-1-(2,2,2-trifluoroethyl)pyridin-4(1H)-one (820 mg, 2.8 mmol) was mixed with 10% palladium on charcoal (wet, 84 mg) in methanol (20 mL). The mixture was stirred at room temperature under hydrogen at 30 psi in a Parr apparatus for 35 minutes. The mixture was filtered through Celite™ and the filtrate was concentrated. The residue was triturated with ether to give 3-hydroxy-2-methyl-1-(2,2,2-trifluoroethyl)pyridin-4(1H)-one (511 mg) as off-white solid. Yield=89%; 1H NMR (DMSO-D6, 90 MHz) δ (ppm): 7.60 (d, J=7.4 Hz, 1H), 6.20 (d, J=7.4 Hz, 1H), 4.99 (q, J=8.8 Hz, 2H) and 2.29 (s, 3H).

Workup

  1. filtrationThe mixture was filtered through Celite™
  2. concentrationthe filtrate was concentrated
  3. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-47d38ac14c1e45939826068ddd01760f
Source dataset
uspto-grants-2015_07
Patent number
US09073865B2

Reaction notes

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