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

HRID 847520
Notes
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Reaction equation

HRID 847520 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 23938PalladiumCatalyst
HCID 176
Acetic Acid
Solvent

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-c4b9051efa674b04a8db050f05eeeaa5
Source dataset
uspto-grants-1992_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05141945

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes