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

HRID 1681752Notes

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]=3

Participants

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-31f6e45db3484271a461a8ace143d8f5
Source dataset: uspto-grants-1992_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05173493

Reaction notes

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