Formic Acid → HCID 15286073, compound

HRID 441000Notes

Reaction equation

HRID 441000 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C@@H:13]([CH3:14])[C@@H:12]([CH2:15][O:16][C:17]3[CH:24]=[CH:23][C:20]([C:21]#N)=[CH:19][CH:18]=3)[O:11][C:10]2=[O:25])=[CH:5][CH:4]=1.C(O)=[O:27]>[Ni]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C@@H:13]([CH3:14])[C@@H:12]([CH2:15][O:16][C:17]3[CH:24]=[CH:23][C:20]([CH:21]=[O:27])=[CH:19][CH:18]=3)[O:11][C:10]2=[O:25])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 67732715HCID 67732715, compound

Product 1

HCID 15286073HCID 15286073, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

To a solution of 0.88 g of Compound [82], which had been obtained in Referential Example 12, dissolved in 25 ml of 80% aqueous formic acid, 1.8 g of Raney nickel were added, followed by heating under reflux for 1.5 hours. The reaction mixture was concentrated under reduced pressure. The residue so obtained was extracted with ethyl acetate. The extract was washed with aqueous sodium bicarbonate, dried over anhydrous magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure. The residue was purified by subjecting same to chromatography on a silica gel column using gradient elution with hexane-ethyl acetate, whereby 0.71 g of the title compound was obtained (yield: 80%).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 1.5 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customThe residue so obtained
  5. extractionwas extracted with ethyl acetate
  6. washThe extract was washed with aqueous sodium bicarbonate
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. customThe residue was purified
  11. washelution with hexane-ethyl acetate

Sources & evidence

ORD record
ord-8c1161fa10b442f1b14aba436796e3d6
Source dataset
uspto-grants-1996_05
Patent number
US05521202

Reaction notes

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