Reaktion #417773

Reaktionsgleichung

ethyl-1-pyrrolidineacetate

sodium hydride

ethyl-1-pyrrolidineacetate

xylene

NaH

N,N-dimethylformamide

→

title compound

Ausbeute 60.0%

4-HYDROXY-1-PHENYL-3-(1-PYRROLIDINYL)-1,8-NAPHTHYRIDIN-2-(1H)-ONE

Ausbeute 60.0%

Lösungsmittel

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture is heated to a temperature
2. 2
   Sonstigeranging between 85-95 degrees Centigrade
3. 3
   workup.ADDITIONis slowly added over a period of 10 minutes
4. 4
   TemperaturThe reaction mixture is heated for 1 to 3 hours
5. 5
   workup.ADDITIONaddition of the aliquots
6. 6
   Sonstigequenched with a slow addition of glacial acetic acid
7. 7
   workup.ADDITIONwater is added
8. 8
   FiltrationThe product is filtered
9. 9
   Waschenwashed with water, acetone, methylene chloride, and acetone
10. 10
    SonstigeThe solid then obtained
11. 11
    Sonstigeis dried in vacuo

Vorschrift

To a solution of 1.5 g (6.5 mM) 2-anilinonicotinic acid, methylester, in dry xylenes at room temperature is added 0.69 g (14.54 M) of sodium hydride (NaH) (50 percent (%) oil emulsion) followed by addition of a small amount of N,N-dimethylformamide (DMF). The reaction mixture is heated to a temperature ranging between 85-95 degrees Centigrade (°C.) and 1.05 milliliters (mL) (6.5 mM) of ethyl-1-pyrrolidineacetate in xylene is slowly added over a period of 10 minutes. The reaction mixture is heated for 1 to 3 hours prior to the addition of aliquots of 0.32 g NaH followed by 1.05 mL of ethyl-1-pyrrolidineacetate as described above (total 3 aliquots). Following addition of the aliquots, the reaction mixture is cooled to 0° C., quenched with a slow addition of glacial acetic acid, and then water is added. The product is filtered and washed with water, acetone, methylene chloride, and acetone. The solid then obtained is dried in vacuo to give 1.20 g (60% yield) of title compound, a white solid.

Quelle