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
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
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