Methyl 3-methoxyisonicotinate → 3-Methoxypyridine-4-carbaldehyde

To an cooled solution (−78° C. internal temp) of 0.192 g of methyl 3-methoxyisonicotinate in 10 mL of toluene was added 2 mL of 1 M diisobutyl aluminum hydride in toluene. After stirring 10 min the reaction was quenched with 5 mL of methanol and concentrated under reduced pressure. To a stirred solution of the residue (0.15 g) in 50 mL of dichloromethane was added 1 mL of water, then 1 g of MgSO4. The mixture was filtered and 0.75 g of activated MnO2 was added. The mixture was heated to reflux under nitrogen for 5 h, then cooled and filtered. Concentration under reduced pressure gave a resin: MS (m+1)=138.1.

1. customwas quenched with 5 mL of methanol
2. concentrationconcentrated under reduced pressure
3. additionTo a stirred solution of the residue (0.15 g) in 50 mL of dichloromethane was added 1 mL of water
4. filtrationThe mixture was filtered
5. addition0.75 g of activated MnO2 was added
6. temperatureThe mixture was heated
7. temperatureto reflux under nitrogen for 5 h
8. temperaturecooled
9. filtrationfiltered
10. concentrationConcentration under reduced pressure
11. customgave a resin

ORD record

ord-677989c6a8a644769bfaeac5bb1789d3

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07855201B2