Ethanol → Ethyl 3-methylpyridine-2-carboxylate

HRID 919779Notes

Reaction equation

HRID 919779 reaction equation
[CH3:1][C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.S(Cl)(Cl)=O.[CH3:15][CH2:16]O>>[CH2:15]([O:9][C:8]([C:3]1[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N:4]=1)=[O:10])[CH3:16]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 2687573-Methylpicolinic acid

Product 1

HCID 12243768Ethyl 3-methylpyridine-2-carboxylate

Conditions

Temperature
-20 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-cdaa3a4ca20c4a21bc6fb50c2f1481f4
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

Loading…