Ammonium formate → 10-ethyl-8,9-dihydro-7-[(5-methyl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one

HRID 486213Notes

Reaction equation

HRID 486213 reaction equation
[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]2[C:12](=[O:42])[C:13](=[CH:16][C:17]3[N:18]=[CH:19][N:20](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[C:21]=3[CH3:22])[CH2:14][CH2:15][C:4]=12)[CH3:2].C([O-])=O.[NH4+]>[Pd].C(O)(=O)C>[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]2[C:12](=[O:42])[CH:13]([CH2:16][C:17]3[N:18]=[CH:19][NH:20][C:21]=3[CH3:22])[CH2:14][CH2:15][C:4]=12)[CH3:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 5444750210-ethyl-8,9-dihydro-7-[(5-methyl-1-trityl-1H-imidazol-4-yl)methylene]pyrido[1,2-a]indol-6(7H)-one

Product 1

HCID 1172276110-ethyl-8,9-dihydro-7-[(5-methyl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-oneYield 56.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 10-ethyl-8,9-dihydro-7-[(5-methyl-1-trityl-1H-imidazol-4-yl)methylene]pyrido[1,2-a]indol-6(7H)-one (1.0 g), 10% palladium on carbon (0.25 g), and ammonium formate (0.5 g) in acetic acid (14 ml) was stirred at 90° C. for 1 hour and 45 minutes and cooled to room temperature. After filtration of the catalyst, the filtrate was evaporated in vacuo and the residue was suspended in 0.5N hydrochloric acid. The aqueous layer was washed twice with toluene, made basic with aqueous sodium bicarbonate solution, and extracted three times with chloroform. The chloroform layer was washed with water twice and brine, dried over anhydrous magnesium sulfate, and evaporated to give crystals. Recrystallization from chloroform-methanol gave 10-ethyl-8,9-dihydro-7-[(5-methyl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one (0.319 g).

Workup

  1. temperaturecooled to room temperature
  2. filtrationAfter filtration of the catalyst
  3. customthe filtrate was evaporated in vacuo
  4. washThe aqueous layer was washed twice with toluene
  5. extractionextracted three times with chloroform
  6. washThe chloroform layer was washed with water twice
  7. dry with materialbrine, dried over anhydrous magnesium sulfate
  8. customevaporated
  9. customto give crystals
  10. customRecrystallization from chloroform-methanol

Sources & evidence

ORD record
ord-09b95e49a96d439aa66b1876c13bcc1a
Source dataset
uspto-grants-1994_03
Patent number
US05290785

Reaction notes

Loading…