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

HRID 969574Notes

Reaction equation

HRID 969574 reaction equation
[OH:1][C:2]1[N:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[CH:4]=O.C([O-])=O.[Na+].Cl.[NH2:19]O>C(O)=O>[OH:1][C:2]1[N:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[C:4]#[N:19]

Participants

5

Reactant 3

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

Product 1

HCID 148370202-Oxo-5-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrileYield 90%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 2-hydroxy-5-(trifluoromethyl)nicotinaldehyde (3.80 g, 17.9 mmol) (approx. 90% purity), sodium formate (1.46 g, 20.8 mmol), hydroxylamine hydrochloride (1.47 g, 20.8 mmol) in formic acid (36.6 mL) was stirred at room temperature for 2 h (cloudy brown solution) and then heated to reflux overnight (first clear brown solution, then cloudy again). After being cooled to room temperature, the reaction mixture was quenched with water and extracted with EtOAc three times. The combined organic layers were washed with water, dried over MgSO4, filtered, and concentrated in vacuo to yield 3.03 grams (90%) of the desired crude product (approx. 75% purity) as a brown solid. MS calculated for C7H3F3N2O: (M+H)+189; found 189.0.

Workup

  1. temperatureheated
  2. temperatureto reflux overnight (first clear brown solution
  3. temperatureAfter being cooled to room temperature
  4. customthe reaction mixture was quenched with water
  5. extractionextracted with EtOAc three times
  6. washThe combined organic layers were washed with water
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ad2f30378cab4669859e1d97aa23987b
Source dataset
uspto-grants-2007_12
Patent number
US07307086B2

Reaction notes

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