Ammonium Acetate → 4-Methyl-6-(trifluoromethyl)pyridin-2(1H)-one

HRID 1426362Notes

Reaction equation

HRID 1426362 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[O:5][C:4](=O)[CH:3]=1.C([O-])(=O)C.[NH4+:17]>C(O)(=O)C>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[NH:17][C:4](=[O:5])[CH:3]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 53404370HCID 53404370, compound

Product 1

HCID 100351414-Methyl-6-(trifluoromethyl)pyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of crude 4-methyl-6-(trifluoromethyl)-2H-pyran-2-one (28.8 g, 162 mmol) in acetic acid (330 mL) was added ammonium acetate (25.0 g, 324 mmol). The reaction solution was heated at 120° C. over weekend. The solvent was removed in vacuo. The residue was diluted with ethyl acetate and washed with saturated NaHCO3 and brine, dried over Na2SC4, filtered and concentrated. The crude was purified with pad silica gel. The solvent was removed. The solid was washed with 10:1 hexanes/ethyl acetate to give the desired product as white solid. LCMS (M+H)+: 178.0.

Workup

  1. customThe solvent was removed in vacuo
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed with saturated NaHCO3 and brine
  4. dry with materialdried over Na2SC4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude was purified with pad silica gel
  8. customThe solvent was removed
  9. washThe solid was washed with 10:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-d06be6ba2b6a411889888009396e8f32
Source dataset
uspto-grants-2015_01
Patent number
US08933085B2

Reaction notes

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