3-OXO-3-(3-PYRIDINYL)PROPANENITRILE synthesis
- Product Name:3-OXO-3-(3-PYRIDINYL)PROPANENITRILE
- CAS Number:30510-18-0
- Molecular formula:C8H6N2O
- Molecular Weight:146.15
93-60-7
75-05-8
30510-18-0
To a stirred solution of methyl nicotinate (XVIII; 8 g; 58 mmol) in toluene (110 mL) at 0 °C was slowly added sodium hydride (2.8 g; 110 mmol). The reaction mixture was kept stirred at 0 °C for 30 min, followed by dropwise addition of acetonitrile (12 g; 91 mmol). The reaction mixture was heated to reflux for 72 hours. After completion of the reaction, the mixture was cooled, concentrated under reduced pressure and diluted with ice-cold water. The pH of the reaction mixture was adjusted to acidic with glacial acetic acid. Subsequently, the aqueous layer was extracted with ethyl acetate (3 x 100 mL). The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 3-oxo-3-(pyridin-3-yl)propanenitrile (XIX; 6 g, 70% yield) as a yellow solid. Mass spectrometry analysis showed [M-1]? peak at 145.01.
Yield:30510-18-0 70%
Reaction Conditions:
Stage #1: methyl 3-pyridinecarboxylatewith sodium hydride in toluene at 0; for 0.5 h;
Stage #2: acetonitrile in toluene; for 72 h;Reflux;
Steps:
4 Synthesis of XIX:
To a stirred solution of methyl nicotinate (XVIII; 8 g; 58 mmol) in toluene (110 mL) was added sodium hydride (2.8 g; 110 mmol) at 0°C. The reaction mixture was stirred at 0°C for 30 minutes and then acetonitrile (12 g; 91 mmol) was added. The reaction mixture was heated to a reflux for 72 hours. The reaction mixture was cooled, concentrated at reduced pressure and diluted with ice cold water. The reaction mixture was acidified using glacial acetic acid. Theaqueous layer was extracted with ethyl acetate (3 x 100 mL). The combined organic layers were washed with brine, dried over Na2504, filtered and concentrated under vacuum to afford 3-oxo-3-(pyridin-3-yl)propanenitrile as a yellow solid (XIX; 6 g, 70% yield). MS (M-1):145.01.
References:
WO2015/97122,2015,A1 Location in patent:Page/Page column 81; 82
59-67-6
1128 suppliers
$7.00/25g
30510-18-0
112 suppliers
inquiry
614-18-6
478 suppliers
$5.00/10g
30510-18-0
112 suppliers
inquiry