Ammonium formate → FK 1052

HRID 847515Notes

Reaction equation

HRID 847515 reaction equation
O[CH:2]([C:18]1[N:19]=[CH:20][N:21](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:22]=1[CH3:23])[CH:3]1[C:16](=[O:17])[N:7]2[C:8]3[C:13]([C:14]([CH3:15])=[C:6]2[CH2:5][CH2:4]1)=[CH:12][CH:11]=[CH:10][CH:9]=3.C([O-])=O.[NH4+]>C(O)(=O)C.[Pd]>[CH3:15][C:14]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]2[C:16](=[O:17])[CH:3]([CH2:2][C:18]3[N:19]=[CH:20][NH:21][C:22]=3[CH3:23])[CH2:4][CH2:5][C:6]=12

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 150519238,9-dihydro-7-[(hydroxy)(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]-10-methylpyrido[1,2-a]indol-6(7H)-one

Product 1

HCID 125368FK 1052Yield 76.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 8,9-dihydro-7-[(hydroxy)(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]-10-methylpyrido[1,2-a]-indol-6(7H)-one (4.6 g) in acetic acid (92 ml) were added 10% palladium on carbon (2.3 g) and ammonium formate (7.89 g), and the mixture was refluxed gently for 3 hours. After being cooled, the catalyst was filtered off. The filtrate was evaporated, and diluted with water (50 ml) and diisopropyl ether (50 ml). Aqueous sodium hydroxide was added to neutralized the solution. Resulted precipitates were collected, and washed with water and diisopropyl ether successively, to give 8,9-dihydro-10-methyl-7-[(5-methyl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]-indol-6(7H)-one (1.87 g).

Workup

  1. temperaturethe mixture was refluxed gently for 3 hours
  2. temperatureAfter being cooled
  3. filtrationthe catalyst was filtered off
  4. customThe filtrate was evaporated
  5. additiondiluted with water (50 ml) and diisopropyl ether (50 ml)
  6. additionAqueous sodium hydroxide was added
  7. customResulted
  8. customprecipitates
  9. customwere collected
  10. washwashed with water and diisopropyl ether successively

Sources & evidence

ORD record
ord-2f600e2daab5496ebc5ea58b1fe85b45
Source dataset
uspto-grants-1992_08
Patent number
US05141945

Reaction notes

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