Reaktion #40856

Reaktionsgleichung

(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

Lösungsmittel

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter the addition
2. 2
   SonstigeThe reaction was quenched with water
3. 3
   Extraktionextracted with ethyl acetate
4. 4
   WaschenThe organic layer was washed with water and brine
5. 5
   Trocknendried over MgSO4
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigeThe solid residue was triturated with diethyl ether
8. 8
   Filtrationfiltered
9. 9
   Sonstigedried under high vacuum

Vorschrift

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.

Quelle