Sodium Hydroxide → 6-Amino-4-[4-(2-hydroxyethoxy)phenyl]-2-oxo-1,2-dihydropyridine-3,5-dicarbonitrile
Reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][OH:19])=[CH:12][CH:11]=2)[C:5]([C:20]#[N:21])=[C:4](SC2C=CC=CC=2)[N:3]=1.[OH-:29].[Na+]>C(O)C>[NH2:1][C:2]1[NH:3][C:4](=[O:29])[C:5]([C:20]#[N:21])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][OH:19])=[CH:12][CH:11]=2)[C:7]=1[C:8]#[N:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
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.
Workup
- customa clear solution is formed
- temperatureAfter cooling to RT
- customthe solvent is removed on a rotary evaporator
- customis formed
- stirringThe suspension is stirred at RT for 3 h
- filtrationThe precipitate is filtered off
- washwashed with about 5 ml of water
- customa little ethanol and then recrystallized from about 10 ml of ethanol
- customThe product obtained in this manner
- customis used without further purification in the subsequent reactions
Sources & evidence
- ORD record
- ord-963d645643a140edb98468049189ceca
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09095582B2
Reaction notes
Loading…