Ethanol → Ethyl 3-methylpyridine-2-carboxylate

Temperature

-20 °C

3-Methyl-pyridine-2-carboxylic acid (1 g, 7.29 mmol) was dissolved in EtOH (50 mL) and cooled to −20° C. Thionyl chloride (1.1 mL, 14.6 mmol) was added, and the resulting white suspension was refluxed for 5 h, then concentrated to dryness. Water (10 mL) was added and solid Na2CO3 was added to neutralize the solution. The resulting mixture was extracted with ether. The organic layer was dried over MgSO4, and the solvent was removed by distillation to give 1.25 g of the title compound as an oil. 1H NMR (CDCl3, 200 MHz): δ=8.54 (d, 1H, J=3.9 Hz), 7.59 (d, 1H, J=7.8 Hz), 7.26-7.40 (m, 1H), 4.45 (q, 2H, J=7.0 Hz), 2.59 (s, 3H), 1.45 (t, 3H, J=7.0 Hz).

1. temperaturethe resulting white suspension was refluxed for 5 h
2. concentrationconcentrated to dryness
3. additionWater (10 mL) was added
4. additionsolid Na2CO3 was added
5. extractionThe resulting mixture was extracted with ether
6. dry with materialThe organic layer was dried over MgSO4
7. customthe solvent was removed by distillation

ORD record

ord-373a833ed31247cbba6c2ec6e800dbad

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08921389B2