2-Pyridinecarboxaldehyde → HCID 86744857, compound

HRID 1493842Notes

Reaction equation

HRID 1493842 reaction equation
[C:1]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:5])[CH:2]([CH3:4])[CH3:3].[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]=O>C1C=CC=CC=1.C(O)(=O)C.N1CCCCC1>[CH3:3][CH:2]([CH3:4])[C:1](=[O:5])[C:6](=[CH:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][N:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

6

Reactant 2

HCID 142732-PyridinecarboxaldehydeHCID 81583Ethyl isobutyrylacetate

Product 1

HCID 86744857HCID 86744857, compoundYield 83.6%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 8082PiperidineCatalystHCID 241BenzeneSolvent

Procedure

To a solution of ethyl isobutyrylacetate (15.78 g, 99.7 mmol) and pyridine-2-carboxaldehyde (10.7 g, 99.9 mmol) in dry benzene (100 mL) at room temperature under argon was added acetic acid (0.30 mL, 5.2 mmol) and piperidine (0.80 mL, 8.1 mmol). After stirring at room temperature for 1 hour and at reflux for 3 hours, the cooled mixture was washed with water, saturated NaHCO3 and saturated NaCl solutions, dried (Na2SO4) and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel eluting with ethyl acetate (EtOAc)-hexane (1:9) to give title compound (20.61 g, 83%) as an orange, viscous oil which crystallized on standing to a semi-solid mass, mp 53°-55° C.

Workup

  1. temperatureat reflux for 3 hours
  2. washthe cooled mixture was washed with water, saturated NaHCO3 and saturated NaCl solutions
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash chromatography on silica gel eluting with ethyl acetate (EtOAc)-hexane (1:9)

Sources & evidence

ORD record
ord-33364260bb20445a9ef62d2e0366f2d5
Source dataset
uspto-grants-1991_06
Patent number
US05025000

Reaction notes

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