Water → 2-Oxo-5-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile

HRID 981043Notes

Reaction equation

HRID 981043 reaction equation
[CH:1]([C:3]1[C:4](=[O:13])[NH:5][CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1)=O.Cl.[NH2:15]O.C([O-])=O.[Na+].O>C(O)=O>[C:1]([C:3]1[C:4](=[O:13])[NH:5][CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1)#[N:15]

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 2723810Sodium FormateHCID 198196692-Oxo-5-(trifluoromethyl)-1,2-dihydropyridine-3-carbaldehyde

Product 1

HCID 148370202-Oxo-5-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 3-formyl-5-trifluoromethyl-2-pyridone (3.5 g), hydroxylamine hydrochloride (1.42 g) and sodium formate (1.39 g) in 98% formic acid (42 ml) was heated to reflux for a period of 20hrs. After cooling to ambient temperature, the reaction mixture was poured into water, and rigorously extracted with ethyl acetate. The combined organic extracts were washed with saturated aqueous sodium bicarbonate solution, followed by brine, and dried over anhydrous magnesum sulphate. Removal of the solvent under reduced pressure gave 3-cyano-5-trifluoromethyl-2pyridone as an off-white solid (m.p. 170-175° C.) which was used without further purification. The compound showed (DMSO) 8.54 (1H,d) 8.30 (1H,d).

Workup

  1. temperatureto reflux for a period of 20hrs
  2. extractionrigorously extracted with ethyl acetate
  3. washThe combined organic extracts were washed with saturated aqueous sodium bicarbonate solution
  4. dry with materialdried over anhydrous magnesum sulphate
  5. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-7f2a1838bf964afa89a0cca27bdeaa90
Source dataset
uspto-grants-1991_02
Patent number
US04990512

Reaction notes

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