Sodium Hydroxide → 2-(3-Formyl-2-methoxyphenoxy)-6-(trifluoromethyl)nicotinonitrile

HRID 1178499Notes

Reaction equation

HRID 1178499 reaction equation
Cl[C:2]1[N:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[OH:14][C:15]1[C:16]([O:23][CH3:24])=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=[O:19].[F-].[K+].[OH-].[Na+]>CN(C=O)C>[CH:18]([C:17]1[C:16]([O:23][CH3:24])=[C:15]([CH:22]=[CH:21][CH:20]=1)[O:14][C:2]1[N:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5])=[O:19]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 522689Potassium FluorideHCID 27784132-Chloro-6-(trifluoromethyl)nicotinonitrileHCID 118049533-Hydroxy-2-methoxybenzaldehyde

Product 1

HCID 219303952-(3-Formyl-2-methoxyphenoxy)-6-(trifluoromethyl)nicotinonitrileYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloro-6-(trifluoromethyl)nicotinonitrile (0.34 g, 1.6 mmol), 3-hydroxy-2-methoxybenzaldehyde (0.25 g, 1.6 mmol) and potassium fluoride (0.29 g, 4.9 mmol) were heated with stirring in dry DMF (4 mL) at 120° C. for 3 h. The reaction mixture was cooled, poured into 1N sodium hydroxide solution and extracted with ethyl acetate. The ethyl acetate layer was separated, washed with 1N sodium hydroxide solution (3×), water (3×), brine (1×), and dried over MgSO4. After filtration, the solvent was removed in vacuo to yield 2-(3-formyl-2-methoxyphenoxy)-6-(trifluoromethyl)nicotinonitrile (0.50 g, 94%) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. customThe ethyl acetate layer was separated
  4. washwashed with 1N sodium hydroxide solution (3×), water (3×), brine (1×)
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-2c17f943fafc4b58bd3a92c4b698d2f9
Source dataset
uspto-grants-2007_10
Patent number
US07276528B2

Reaction notes

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