Formic Acid → HCID 86640047, compound

HRID 452795Notes

Reaction equation

HRID 452795 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]3[O:14][CH:13]=[C:12]([C:15]#N)[C:11]=3[CH:17]=2)=[N:4][N:3]=1.C(O)=[O:19]>[Ni].O>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]3[O:14][CH:13]=[C:12]([CH:15]=[O:19])[C:11]=3[CH:17]=2)=[N:4][N:3]=1

Participants

5

Reactant 2

HCID 284Formic AcidHCID 68663454HCID 68663454, compound

Product 1

HCID 86640047HCID 86640047, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

A mixture of 5-(5-methyl-1,3,4-oxadiazol-2-yl)-1-benzofuran-3-carbonitrile (1.00 g, 4.44 mmol), Raney-nickel (2.0 g), formic acid (16 mL) and water (4 mL) was heated under reflux for 30 min. After cooling, the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was diluted with ethyl acetate, washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/tetrahydrofuran=1/1) and recrystallized from hexane/tetrahydrofuran to give the title compound (558 mg, yield 55%) as colorless crystals.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 min
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionThe residue was diluted with ethyl acetate
  7. washwashed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (hexane/tetrahydrofuran=1/1)
  11. customrecrystallized from hexane/tetrahydrofuran

Sources & evidence

ORD record
ord-e8c3b2102818492e869254727e2012a8
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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