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

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.

1. customThe reaction contents
2. filtrationwere filtered through a pad of celite and methanol
3. customwas removed in vacuo
4. extractionextracted
5. washThe organic phase was washed with brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. custompurified by gradient elution on silica gel (0 to 12% MeOH (10% NH4OH) in DCM)

ORD record

ord-747e9ef7c7b847af96f01f216c99b779

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08703770B2