Reacción #315423

Ecuación de reacción

water

4-hydroxy-3-methyl-benzaldehyde

6-chloro-nicotinonitrile

potassium carbonate

→

title compound

Rendimiento 89.4%

6-(4-Formyl-2-methyl-phenoxy)-nicotinonitrile

Rendimiento 89.4%

Disolventes

dimethylacetamide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONdilute
2. 2
   Extracciónextract with ethyl acetate (3×50 mL)
3. 3
   LavadoWash
4. 4
   Secadodry over anhydrous magnesium sulfate
5. 5
   Filtraciónfilter
6. 6
   Concentraciónconcentrate
7. 7
   OtroPurify the residue by silica gel chromatography (hexanes→ethyl acetate gradient/1.5 L)

Procedimiento

Combine 4-hydroxy-3-methyl-benzaldehyde (0.502 g, 3.69 mmol), 6-chloro-nicotinonitrile (0.510 g, 3.68 mmol), and potassium carbonate (1.28 g, 9.26 mmol) in dimethylacetamide (18 mL) and warm to 100° C. After 1 h. cool to ambient temperature, dilute reaction mixture with water (40 mL), and extract with ethyl acetate (3×50 mL). Wash combined organic extracts with water and brine successively, dry over anhydrous magnesium sulfate, filter, and concentrate. Purify the residue by silica gel chromatography (hexanes→ethyl acetate gradient/1.5 L) to provide 0.784 g (89%) of the title compound as a light brown solid: mass spectrum (electrospray): m/z=239.0 (M+1); 1H NMR (CDCl3): 10.01 (s, 1H), 8.44 (d, 1H, J=2.4 Hz), 7.99 (dd, 1H, J=2.0, 8.3 Hz), 7.86 (s, 1H), 7.81 (dd, 1H, J=1.5, 8.3 Hz), 7.23 (d, 1H, J=8.3 Hz), 7.13 (d, 1H, J=8.8 Hz), 2.25 (s, 3H).

Fuente