2-ACETYL-ISONICOTINONITRILE synthesis
- Product Name:2-ACETYL-ISONICOTINONITRILE
- CAS Number:37398-49-5
- Molecular formula:C8H6N2O
- Molecular Weight:146.15
Yield:37398-49-5 71.9%
Reaction Conditions:
with ammonium peroxydisulfate;sulfuric acid;silver nitrate in dichloromethane;water;Reflux;
Steps:
1 Step 1 : 2-Acetylisonicotinonitrile
Step 1 : 2-Acetylisonicotinonitrile To a solution of isonicotinonitrile (52 g, 0.5 mol) in dichloromethane (1300 mL) and water (1 100 mL) were added ammonium persulfate ((NH4)2S208) (170 g, 0.75 mol), silver nitrate (6.8 g, 0.04 mol) and aqueous sulfuric acid (40 mL, 98% sulfuric acid in 400 mL). A solution of 3-oxo-butyric acid (1 10 g, 1.25 mol) in dichloromethane (100 mL) was added dropwise while keeping the mixture refluxing. The reaction mixture was refluxed for 2 h. The resulting mixture was basified to pH -8-9 using sodium carbonate powder. The mixture was filtered and the filtrate was extracted with dichloromethane (500 mL x 3). The combined organics were dried over sodium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethanol to afford 2-acetylisonicotinonitrile (52.0 g, 71.9%).
References:
WO2013/150416,2013,A1 Location in patent:Page/Page column 117
