Hydrochloric Acid → 1-(5,6-Dimethoxypyridin-2-yl)methanamine

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Reaction Steps

To a solution of 2,3-dimethoxy-6-cyanopyridine (4-5, 5.1 g, 31.1 mmol) in MeOH (260 mL) was added Pearlman's Catalyst (2.18 g, 3.11 mmol, 20 wt %) and concentrated HCl (20.0 mL, 249 mmol, 12M). The system was then stirred under an atmosphere of hydrogen via a balloon for 1.5 h. The reaction contents were filtered through a pad of celite and methanol was removed in vacuo. The crude mixture was then basified using saturated Na2CO3 and then extracted using 4:1 Chloroform:Ethanol. The organic phase was washed with brine, dried over Na2SO4, filtered and purified by gradient elution on silica gel (0 to 12% MeOH (10% NH4OH) in DCM) to yield the desired product (4-6) as a bone semi-solid. ESI+MS [M+H]+ C8H12N2O2: M-16 (—NH2), 152.06 found, 168.2 required.

Provenance & Evidence