Ammonium formate → FK 1052

HRID 486208Notes

Reaction equation

HRID 486208 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-de13585eda784f92b86c3f4209025953
Source dataset
uspto-grants-1994_03
Patent number
US05290785

Reaction notes

Loading…