Reacción #40856

Ecuación de reacción

(E)-3-(dimethylamino)-1-phenyl-2-p-tolylprop-2-en-1-one

Compound 113

(E)-3-(dimethylamino)-1-phenyl-2-p-tolylprop-2-en-1-one

cyanoacetamide

MeOH

NaH

→

title compound

2-Hydroxy-6-phenyl-5-p-tolylnicotinonitrile

Disolventes

DMF

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONAfter the addition
2. 2
   OtroThe reaction was quenched with water
3. 3
   Extracciónextracted with ethyl acetate
4. 4
   LavadoThe organic layer was washed with water and brine
5. 5
   Secadodried over MgSO4
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   OtroThe solid residue was triturated with diethyl ether
8. 8
   Filtraciónfiltered
9. 9
   Otrodried under high vacuum

Procedimiento

A solution of (E)-3-(dimethylamino)-1-phenyl-2-p-tolylprop-2-en-1-one (Compound 113, 500 mg, 1.9 mmol), cyanoacetamide (175 mg, 2.1 mmol) and MeOH (0.2 ml, 2.2 mmol) in DMF (4 ml) was cannulated into a suspension of NaH (119 mg, 4.7 mmol, 95% in mineral oil) in DMF (2 ml) at room temperature. After the addition was completed, the reaction was heated to 95° C. for 2 hours. The reaction was quenched with water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over MgSO4, concentrated in vacuo. The solid residue was triturated with diethyl ether, filtered and dried under high vacuum to yield the title compound as a white solid.

Fuente