Ethylvanillin → 6-(2-Ethoxy-4-formylphenoxy)nicotinonitrile

HRID 130795

Reaction equation

HRID 130795 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[OH:12])[CH:7]=[O:8])[CH3:2].Cl[C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][N:15]=1.C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:7]=[O:8])[CH:9]=[CH:10][C:11]=1[O:12][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][N:15]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8467EthylvanillinHCID 11430Potassium CarbonateHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 597303196-(2-Ethoxy-4-formylphenoxy)nicotinonitrileYield 93.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Using a method similar to Example 365, step 1, and using 3-ethoxy-4-hydroxy-benzaldehyde (3.00 g, 18.0 mmol), 6-chloro-nicotinonitrile (2.65 g, 18.0 mmol), and potassium carbonate (6.62 g, 45.2 mmol) in dimethylacetamide (90 mL), after 3 h at 100° C. (no purification) provides 4.52 g (93%) of the title compound as a yellow/white solid: mass spectrum (electrospray): m/z=269.0 (M+1); 1H NMR (CDCl3): 9.96 (s, 1H), 8.39 (d, 1H, J=2.0 Hz), 7.95 (dd, 1H, J=2.0, 8.3 Hz), 7.55-7.50 (m, 2H), 7.33 (d, 1H, J=7.8 Hz), 7.11 (d, 1H, J=9.3 Hz), 4.05 (q, 2H, J=6.8 Hz), 1.16 (t, 3H, J=6.8 Hz).

Workup

  1. customafter 3 h at 100° C. (no purification)

Sources & evidence

ORD record
ord-e4fb58fc619c4af0bb5cd54e96ad962f
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Linked notes

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