4-Pyridinepropanenitrile synthesis

10synthesis methods

Product Name:4-Pyridinepropanenitrile
CAS Number:84200-06-6
Molecular formula:C8H8N2
Molecular Weight:132.16

2-Propenenitrile,3-(4-pyridinyl)-,(2E)-(9CI)

123293-72-1
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84200-06-6
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Yield:84200-06-6 96%

Reaction Conditions:

with 10% Pd/C;hydrogen for 15 h;Inert atmosphere;

Steps:

1s’ (0.5 g, 3.8 mmol, 1.0 equiv) was added to a vial containing MeOH (0.4 M). 10% Pd/C (55 mg, 0.64 mmol, 0.15equiv) was then added, and the reaction vial was purged with argon for 20 minutes, followed by purging with hydrogenballoon. The reaction mixture was then equipped with a hydrogen balloon and stirred overnight (~15 h). Afterconsumption of the starting material as indicated by TLC, the reaction mixture was filtered through short Celite plug,concentrated in vacuo, and purified by flash column chromatography using 50%-100% EtOAc in hexane as eluent togive 1s as a yellow oil (0.49 g, 96%). 1H NMR (CDCl3, 400 MHz) 8.59 (d, J = 5.9 Hz, 2H), 7.18 (d, 5.9 Hz, 2H),2.97 (t, J = 7.3 Hz, 2H), 2.67 (t, J = 7.3 Hz, 2H). 13C{1H} NMR (CDCl3, 100 MHz) = 150.5, 146.7, 123.6, 118.5,30.8, 18.3. HRMS (ESI) m/z Calcd for C8H9N2 [M+H]+ 133.0760, found 133.0760.

References:

Shivers, Grant N.;Tun, Soe L.;McLean, Shay L.;Pigge, Chris [Synlett,2022] Location in patent:supporting information

24490-79-7 Synthesis