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

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Reaction Steps

To a solution of 2,3-dimethoxy-6-cyanopyridine (5-5, 5.1 g, 31.1 mmol) in MeOH (260 mL) was added Pearlman's catalyst (2.18 g, 3.11 mmol, 20 weight percent) 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 concentrated to yield the desired product (5-6) as a bone semi-solid. ESI+MS [M+H]+ C8H12N2O2: M-16 (—NH2), 152.06 found, 152.2 required.

Provenance & Evidence