Acetone → HCID 178467987, compound

HRID 85537

Reaction equation

HRID 85537 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]([O:9]CC)=O)=[CH:3][CH:2]=1.[CH3:12][C:13]([CH3:15])=[O:14].C[O-].[Na+]>C1COCC1>[OH:14]/[C:13](/[CH3:15])=[CH:12]\[C:7]([C:4]1[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=1)=[O:9]

Participants

5

Reactant 3

HCID 180AcetoneHCID 15291Ethyl isonicotinateHCID 10942334Sodium Methoxide

Product 1

HCID 178467987HCID 178467987, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-pyridinecarboxylate (30 g, 198 mmol) and acetone (34.58 g, 595 mmol) in THF (150 mL) was slowly added NaOMe (12.87 g, 238 mmol) at 35-40° C. The mixture was stirred at room temperature for 0.5 h, and then heated at reflux for 3 h. The mixture was cooled to room temperature and filtered to give a solid, which was washed with t-BuOMe, and dissolved in H2O. The solution was acidified with acetic acid and the resulting oily product was extracted with CHCl3. The solvent was removed in vacuo, and the crude product was obtained (12 g, 37%) and used without further purification. 1H NMR (400 MHz, DMSO-d6) δ 8.73 (d, 2H), 7.76 (d, 2H), 6.63 (s, 1H), 2.21 (s, 3H); note: enolic OH does not appear.

Workup

  1. customat 35-40° C
  2. temperatureheated
  3. temperatureat reflux for 3 h
  4. temperatureThe mixture was cooled to room temperature
  5. filtrationfiltered
  6. customto give a solid, which
  7. washwas washed with t-BuOMe
  8. dissolutiondissolved in H2O
  9. extractionthe resulting oily product was extracted with CHCl3
  10. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a8e7776ebf4b407281de1ba5212a6fc6
Source dataset
uspto-grants-2014_09
Patent number
US08846935B2

Linked notes

Loading…