Dimethylformamide → 3,5-Dimethoxyisonicotinaldehyde

Temperature

0 °C

To a solution of 3,5-dimethoxypyridine (3.6 g, 25.90 mmol, 1 eq.) in THF (80 mL) was added BuLi (3M/hexanes, 13.0 mL, 38.85 mmol, 1.5 eq.) at −20° C. The mixture was warmed to 0° C., stirred at 0° C. for 30 min, cooled back down to −78° C., and added DMF (3.8 g, 51.8 mmol, 2 eq.). The mixture was gradually warmed to 0° C., quenched with NH4Cl(sat) solution, and diluted with EtOAc. The aqueous layer was extracted with EtOAc twice. The combined organic layers were washed with brine, dried over Na2SO4, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give 3,5-dimethoxyisonicotinaldehyde (2.7 g, 62%) as a yellow solid. LRMS (M+H+) m/z 168.1.

1. temperaturecooled back down to −78° C.
2. temperatureThe mixture was gradually warmed to 0° C.
3. customquenched with NH4Cl(sat) solution
4. additiondiluted with EtOAc
5. extractionThe aqueous layer was extracted with EtOAc twice
6. washThe combined organic layers were washed with brine
7. dry with materialdried over Na2SO4
8. concentrationconcentrated
9. custompurified on silica gel using
10. additiona mixture of EtOAc and hexanes as eluent

ORD record

ord-ef4009862a1f4cb49b0047d5dc47ffb5

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09012450B2