Ammonium Hydroxide → 2-(1,1,1-Trifluoro-2-methylpropan-2-YL)pyridin-4(1H)-one

HRID 1050158Notes

Reaction equation

HRID 1050158 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]([C:6]1O[CH:8]=[CH:9][C:10](=[O:12])[CH:11]=1)([CH3:5])[CH3:4].[NH4+:15].[OH-]>>[F:1][C:2]([F:14])([F:13])[C:3]([C:6]1[NH:15][CH:8]=[CH:9][C:10](=[O:12])[CH:11]=1)([CH3:5])[CH3:4]

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 716828082-(1,1,1-trifluoro-2-methylpropan-2-yl)-4H-pyran-4-one

Product 1

HCID 716828092-(1,1,1-Trifluoro-2-methylpropan-2-YL)pyridin-4(1H)-oneYield 74.7%

Conditions

Temperature
90 °C

Procedure

A mixture of 2-(1,1,1-trifluoro-2-methylpropan-2-yl)-4H-pyran-4-one (800 mg, 3.88 mmol) in NH4OH (8 mL, 205 mmol) was stirred at 90° C. for 1 h. Then the mixture was concentrated, triturated with MeOH (20 mL) and filtered. The filtrate was concentrated and purified by silica column chromatography (DCM/MeOH=9:1). All fractions found to contain product by TLC (DCM/MeOH=9:1, Rf=0.2) were combined and concentrated to yield a yellow oil of 2-(1,1,1-trifluoro-2-methylpropan-2-yl)pyridin-4(1H)-one (700 mg, 2.90 mmol, 74.7% yield): 1H NMR (400 MHz, CD3OD): δ 7.87 (d, J=7.2 Hz, 1H), 6.70 (d, J=2.4 Hz, 1H), 6.54 (dd, J=2.4, 7.2 Hz, 1H), 1.60 (s, 6H). ES-LCMS m/z 206.1 (M+H).

Workup

  1. concentrationThen the mixture was concentrated
  2. customtriturated with MeOH (20 mL)
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica column chromatography (DCM/MeOH=9:1)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-43b6baea6d9a44b6b5dd20e71f03c271
Source dataset
uspto-grants-2016_07
Patent number
US09382238B2

Reaction notes

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