Ammonium formate → HCID 22602609, compound

HRID 2307840Notes

Reaction equation

HRID 2307840 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:9](=[O:10])[O:8][CH:7]2[B:14]([OH:16])[OH:15])([O-])=O.C([O-])=O.[NH4+]>[Pd].O1CCCC1>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:9](=[O:10])[O:8][CH:7]2[B:14]([OH:16])[OH:15]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 22602613HCID 22602613, compound

Product 1

HCID 22602609HCID 22602609, compoundYield 49.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

5-Nitroboronophthalide (2.72 g, 15.2 mmol) and 10% palladium on carbon (911 mg) are suspended in 30 mL of anhydrous tetrahydrofuran. Ammonium formate (4.41 g, 70 mmol) is added and the mixture is stirred at 50° C., under nitrogen for 3 hr. After cooling to room temperature, the catalyst is removed by filtration through a pad of Celite, which is then washed with ˜30 mL of methanol. Concentration in vacuo gives a light brown oil that is purified by dissolution in ethyl acetate and filtration through a plug of silica. Recrystallization from ethanol and water gives a light yellow crystalline solid (1.12 g, 7.52 mmol, 49.5%) with a m.p. of 160-161° C.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe catalyst is removed by filtration through a pad of Celite, which
  3. washis then washed with ˜30 mL of methanol
  4. concentrationConcentration in vacuo
  5. customgives a light brown oil that
  6. customis purified by dissolution in ethyl acetate
  7. filtrationfiltration through a plug of silica
  8. customRecrystallization from ethanol and water

Sources & evidence

ORD record
ord-5e4980dc9e444509b281f23adf384ea5
Source dataset
uspto-grants-2004_12
Patent number
US06833274B2

Reaction notes

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