Sodium Hydroxide → 6-Ethyl-2-(3-formyl-2-methoxy-phenoxy)-nicotinonitrile

HRID 1178508Notes

Reaction equation

HRID 1178508 reaction equation
Cl[C:2]1[N:9]=[C:8]([CH2:10][CH3:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[OH:12][C:13]1[C:14]([O:21][CH3:22])=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=[O:17].[F-].[K+].[OH-].[Na+]>CN(C=O)C>[CH2:10]([C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([O:12][C:13]2[CH:20]=[CH:19][CH:18]=[C:15]([CH:16]=[O:17])[C:14]=2[O:21][CH3:22])[N:9]=1)[CH3:11]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 522689Potassium FluorideHCID 118049533-Hydroxy-2-methoxybenzaldehydeHCID 219304332-Chloro-6-ethylnicotinonitrile

Product 1

HCID 219303926-Ethyl-2-(3-formyl-2-methoxy-phenoxy)-nicotinonitrileYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloro-6-ethylnicotinonitrile (0.27 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 6 h, then at 80° C. for 16 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 (4×), brine (1×), and dried over MgSO4. After filtration, the solvent was removed in vacuo to yield 6-ethyl-2-(3-formyl-2-methoxy-phenoxy)-nicotinonitrile (0.28 g, 61%) as a yellow oil.

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 (4×), brine (1×)
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-4167705300bc451ab81b2d45dff7f9a8
Source dataset
uspto-grants-2007_10
Patent number
US07276528B2

Reaction notes

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