Ethanol → 8,9-dihydro-7-[(5-methyl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one
Reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH:7]=[C:8]1[C:20](=[O:21])[N:12]2[C:13]3[C:18]([CH:19]=[C:11]2[CH2:10][CH2:9]1)=[CH:17][CH:16]=[CH:15][CH:14]=3.C([O-])=O.[NH4+].C(O)C.O1CCCC1>[Pd].O>[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][CH:8]1[C:20](=[O:21])[N:12]2[C:13]3[C:18]([CH:19]=[C:11]2[CH2:10][CH2:9]1)=[CH:17][CH:16]=[CH:15][CH:14]=3Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
To a mixture of 8,9-dihydro-7-[(5-methyl-1H-imidazol-4-yl)methylene]pyrido[1,2-a]indol-6(7H)-one (10.9 g), ammonium formate (17.2 g), ethanol (130 ml), and tetrahydrofuran (110 ml) was added a suspension of 10% palladium on carbon (3.3 g) in water (30 ml). The mixture was heated at 60° C. for 2 hours and then cooled. After filtration of the catalyst, the filtrate was evaporated in vacuo. The residue was dissolved in 10% methanol-chloroform. The organic layer was washed successively with aqueous sodium bicarbonate solution, water, and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The crystalline residue was recrystallized from chloroform-hexane to give 8,9-dihydro-7-[(5-methyl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one (9.85 g).
Workup
- additionwas added
- temperaturecooled
- filtrationAfter filtration of the catalyst
- customthe filtrate was evaporated in vacuo
- dissolutionThe residue was dissolved in 10% methanol-chloroform
- washThe organic layer was washed successively with aqueous sodium bicarbonate solution, water, and brine
- dry with materialdried over anhydrous magnesium sulfate
- customevaporated in vacuo
- customThe crystalline residue was recrystallized from chloroform-hexane
Sources & evidence
- ORD record
- ord-59074a33ea2e4fb58d48dde3329419a6
- Source dataset
- uspto-grants-1994_03
- Patent number
- US05290785
Reaction notes
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