Reaction #595356

Reaction equation

compound

2-Amino-4-[4-(2-hydroxyethoxy)phenyl]-6-(phenylsulfanyl)pyridine-3,5-dicarbonitrile

sodium hydroxide

→

6-Amino-4-[4-(2-hydroxyethoxy)phenyl]-2-oxo-1,2-dihydropyridine-3,5-dicarbonitrile

Solvents

ethanol

Conditions

Workup

1. 1
   Othera clear solution is formed
2. 2
   TemperatureAfter cooling to RT
3. 3
   Otherthe solvent is removed on a rotary evaporator
4. 4
   Otheris formed
5. 5
   workup.STIRRINGThe suspension is stirred at RT for 3 h
6. 6
   FiltrationThe precipitate is filtered off
7. 7
   Washwashed with about 5 ml of water
8. 8
   Othera little ethanol and then recrystallized from about 10 ml of ethanol
9. 9
   OtherThe product obtained in this manner
10. 10
    Otheris used without further purification in the subsequent reactions

Procedure

500 mg (1.29 mmol) of the compound from Example 99A are initially charged in 6.4 ml of ethanol. After addition of 2.57 g (28.96 mmol) of sodium hydroxide, the mixture is stirred at 80° C. for 30 min, and a clear solution is formed. After cooling to RT, the solvent is removed on a rotary evaporator. The residue is taken up in 3 ml of water and acidified with 1 N hydrochloric acid until a yellowish precipitate is formed. The suspension is stirred at RT for 3 h. The precipitate is filtered off, washed with about 5 ml of water and a little ethanol and then recrystallized from about 10 ml of ethanol. The product obtained in this manner is used without further purification in the subsequent reactions.

Source