Acetic Acid → HCID 66815583, compound

HRID 1771520Notes

Reaction equation

HRID 1771520 reaction equation
Cl[C:2]1[N:7]=[C:6]2[CH2:8][CH2:9][O:10][CH2:11][C:5]2=[CH:4][C:3]=1[C:12]#[N:13].C(O)(=O)C>C(O)C.[Zn]>[N:7]1[CH:2]=[C:3]([C:12]#[N:13])[CH:4]=[C:5]2[CH2:11][O:10][CH2:9][CH2:8][C:6]=12

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 616589142-chloro-7,8-dihydro-5H-pyrano[4,3-b]pyridine-3-carbonitrile

Product 1

HCID 66815583HCID 66815583, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

step 3 2-Chloro-7,8-dihydro-5H-pyrano[4,3-b]pyridine-3-carbonitrile (1.77 g, 9.09 mmol) obtained in step 2 was dissolved in ethanol (30 mL), acetic acid (9 mL) and zinc (2.60 g) were added thereto, and the mixture was stirred with heating under reflux for 4 hr. The mixture was allowed to cool to room temperature, then filtered through Celite, and the filtrate was concentrated under reduced pressure. To the obtained residue was added a saturated aqueous sodium hydrogen carbonate solution and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:50) to give 7,8-dihydro-5H-pyrano[4,3-b]pyridine-3-carbonitrile (1.06 g, 73%) as a white solid.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 4 hr
  3. filtrationfiltered through Celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionTo the obtained residue was added a saturated aqueous sodium hydrogen carbonate solution
  6. extractionthe mixture was extracted with chloroform
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:50)

Sources & evidence

ORD record
ord-1f833bdbd44d4ed3a9e31451f2fb2467
Source dataset
uspto-grants-2016_02
Patent number
US09249135B2

Reaction notes

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