Ammonium formate → HCID 19423539, compound

HRID 743056Notes

Reaction equation

HRID 743056 reaction equation
C([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][N:14]1[CH:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][C:15]1=[O:30])C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[C].[Pd]>[NH:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][N:14]1[CH:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][C:15]1=[O:30]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 19423530HCID 19423530, compound

Product 1

HCID 19423539HCID 19423539, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of 15.98 g (40.2 mmol) of 3-(1-benzylpyrrolidin-2-yl)methyl-4-phenyl-3,4-dihydro-2(1H)-quinazolinone in 300 mL ethanol were added 13.61 g (216 mmol) of ammonium formate and 1.64 g of 10 % palladium-carbon, and the mixture was heated under reflux for 5 hours. After being cooled, the reaction mixture was filtered through cerite, and the filtrate was concentrated in vacuo. To the residue was added an aqueous saturated sodium hydrogencarbonate solution, and the mixture was extracted with chloroform. The organic layer separated was dried on potassium carbonate, and then concentrated in vacuo. The residue was purified by means of column chromatography (silica gel, 5:100:900 aqueous ammonia methanol:chloroform) to give 9.32 g (30.3 mmol) of the title compound as an about 1:1 mixture of the diastereomers.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. temperatureAfter being cooled
  4. filtrationthe reaction mixture was filtered through cerite, and the filtrate
  5. concentrationwas concentrated in vacuo
  6. additionTo the residue was added an aqueous saturated sodium hydrogencarbonate solution
  7. extractionthe mixture was extracted with chloroform
  8. customThe organic layer separated
  9. customwas dried on potassium carbonate
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by means of column chromatography (silica gel, 5:100:900 aqueous ammonia methanol:chloroform)

Sources & evidence

ORD record
ord-0502ae6903bf4d0aa59e0e845e98fb93
Source dataset
uspto-grants-1996_09
Patent number
US05556860

Reaction notes

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