(2E)-3-(2-hydroxyphenyl)-1-pyridin-3-ylprop-2-en-1-one synthesis

Yield:18455-64-6 73%

Reaction Conditions:

Stage #1: methyl-3-pyridylketone;salicylaldehydewith sodium hydroxide in water at 0; for 2.83333 h;
Stage #2: with hydrogenchloride in ethanol;water; pH=3;

Steps:

1 (2E)-3-(2-hydroxyphenyl)-1-pyridin-3-ylprop-2-en-1-one

(2E)-3-(2-hydroxyphenyl)-1-pyridin-3-ylprop-2-en-1-one To a vigorously stirred solution of salicylaldehyde (45 mL, 0.42 mol) in 2.5 M NaOH (330 mL) at 0° C. was added 1-(pyridin-3-yl)ethanone (46.2 mL, 0.422 mol) dropwise over 50 min. After stirring at 0° C. for 2 h, the reaction mixture was diluted with water (150 mL) and EtOH (150 mL). The mixture was acidified with conc. HCl to pH=3. The resulting yellow solid was filtered and dried to give (2E)-3-(2-hydroxyphenyl)-1-pyridin-3-ylprop-2-en-1-one (69.8 g, 73%) which was used without further purification. LCMS: (FA) ES+226.2, ES-224.2.

References:

US2008/171754,2008,A1 Location in patent:Page/Page column 91