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

HRID 1031127Notes

Reaction equation

HRID 1031127 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 (3.5g) (UK Application No. 89310162.6), hydroxylamine hydrochloride (1.42g) and sodium formate (1.39g) in 98% formic acid (42ml) was heated to reflux for a period of 20 hours. 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 magnesium sulphate. Removal of the solvent under reduced pressure gave 3-cyano-5-trifluoromethyl-2-pyridone as an off-white solid which was used without further purification.

Workup

  1. temperatureto reflux for a period of 20 hours
  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 magnesium sulphate
  5. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-0ceb31faf03640279030ee5124879cc2
Source dataset
uspto-grants-1992_04
Patent number
US05109004

Reaction notes

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