Reaction #40856

Reaction equation

(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

Solvents

DMF

DMF

Conditions

Workup

1. 1
   workup.ADDITIONAfter the addition
2. 2
   OtherThe reaction was quenched with water
3. 3
   Extractionextracted with ethyl acetate
4. 4
   WashThe organic layer was washed with water and brine
5. 5
   Dryingdried over MgSO4
6. 6
   Concentrationconcentrated in vacuo
7. 7
   OtherThe solid residue was triturated with diethyl ether
8. 8
   Filtrationfiltered
9. 9
   Otherdried under high vacuum

Procedure

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.

Source