Reaktion #4876

Reaktionsgleichung

sodium acetate

1-methyl-3-pyrrolidinol

sodium hydride

2-chloronicotinic acid

→

Sodium 2-[(1-methyl-3-pyrrolidinyl)oxy]-3-pyridinecarboxylate

Lösungsmittel

dimethylsulfoxide

dimethylsulfoxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONDuring addition
2. 2
   Sonstigerose from 25° C. to 31° C
3. 3
   Sonstigereached 55° C.
4. 4
   Temperaturit was maintained there by the intermittent use of an ice bath until addition
5. 5
   TemperaturThe mixture was then heated to 55°-60° C. for 1.5 hr
6. 6
   Temperatur, cooled
7. 7
   Filtrationfiltered
8. 8
   Filtrationfiltered
9. 9
   SonstigeThe solid was recrystallized from ethyl acetatemethanol
10. 10
    Sonstige240° C

Vorschrift

To a stirred suspension of 6.4 g (0.13 mole) of 50% sodium hydride (mineral oil) in 50 ml of dimethylsulfoxide was added dropwise 6.4 g (0.063 mole) of 1-methyl-3-pyrrolidinol. During addition, the temperature rose from 25° C. to 31° C. After 10 minutes, a solution of 10 g (0.063 mole) of 2-chloronicotinic acid in 50 ml of dimethylsulfoxide was added dropwise causing the temperature to rise. When the temperature reached 55° C., it was maintained there by the intermittent use of an ice bath until addition was complete. The mixture was then heated to 55°-60° C. for 1.5 hr., cooled and filtered. The filter cake was suspended in 100 ml of ethyl acetate and filtered. The solid was recrystallized from ethyl acetatemethanol. Yield of product was 5 g., dec. 240° C. The NMR analysis showed that the compound contained 1/3 mole of sodium acetate as impurity.

Quelle