α-Formyl-3-pyridineacetonitrile → HCID 23122145, compound

HRID 225510Notes

Reaction equation

HRID 225510 reaction equation
[CH3:1][O:2][C:3]([CH2:5][NH:6][CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:4].O=[CH:15][CH:16]([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)[C:17]#[N:18]>C(O)(=O)C>[C:17](/[C:16](/[C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)=[CH:15]\[N:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])#[N:18]

Participants

4

Reactant 2

HCID 23336303α-Formyl-3-pyridineacetonitrileHCID 43174172HCID 43174172, compound

Product 1

HCID 23122145HCID 23122145, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

To an acetic acid (30 mL) solution of ethyl 3-{[(methoxycarbonyl)methyl]amino}propanate (6.720 g) was added a crude product of 3-oxo-2-(3-pyridyl)propanenitrile (7.826 g), and the mixture was stirred at 80° C. for 2 days. The reaction solution was cooled to room temperature, and the solvent was distilled off under reduced pressure. The residue was diluted with water, and sodium carbonate was added thereto for neutralization, followed by extracting the solution with ethyl acetate. The organic layer was washed with saturated brine, and dried over sodium sulfate, which was then filtered for separation. Thereafter, the solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=1/3), to obtain the title compound (7.521 g, yield 83%). The ESI/MS data of the compound are given below.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionThe residue was diluted with water, and sodium carbonate
  4. additionwas added
  5. extractionby extracting the solution with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over sodium sulfate, which
  8. filtrationwas then filtered for separation
  9. distillationThereafter, the solvent was distilled off under reduced pressure
  10. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=1/3)

Sources & evidence

ORD record
ord-81037738e25f47dfaf52ac97195adb7e
Source dataset
uspto-grants-2009_07
Patent number
US07557113B2

Reaction notes

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