Ethanol → 7-Chloro-3-(1-imidazolylmethyl)-2-methylimidazo[2,1-a]isoquinoline

HRID 649152Notes

Reaction equation

C(O)C.COS([O-])(=O)=O.[Cl:10][C:11]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:12]=1[CH:13]=[CH:14][N:15]1[C:23]([CH2:24][N+](C)(C)C)=[C:22]([CH3:29])[N:21]=[C:16]12.[NH:30]1[CH:34]=[CH:33][N:32]=[CH:31]1>CS(C)=O>[Cl:10][C:11]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:12]=1[CH:13]=[CH:14][N:15]1[C:23]([CH2:24][C:31]3[NH:30][CH:34]=[CH:33][N:32]=3)=[C:22]([CH3:29])[N:21]=[C:16]12

Participants

Conditions

Temperature: 100 °C

Procedure

Ethanol (50 ml) was added to a mixture of 7-chloro-2-methyl-3-trimethylammoniomethylimidazo[2,1-a]isoquinoline methylsulfate (2.3 g) and imidazole (0.95 g) in dimethyl sulfoxide (20 ml) and heated at 100° C. with stirring for 5 hours. After the removal of ethanol by distillation, the residue was poured into water. The resulting precipitates were collected by filtration, dried and recrystallized from ethyl acetate. The obtained crystals were chromatographed on silica gel (16 g) with a mixture of chloroform and methanol (10:1) as an eluent. The eluates were evaporated in vacuo and the residual solid was recrystallized from ethyl acetate to give 7-chloro-3-(1-imidazolylmethyl)-2-methylimidazo[2,1-a]isoquinoline (0.7 g).

Workup

customAfter the removal of ethanol
distillationby distillation
additionthe residue was poured into water
customThe resulting precipitates
filtrationwere collected by filtration
customdried
customrecrystallized from ethyl acetate
customThe obtained crystals were chromatographed on silica gel (16 g) with a mixture of chloroform and methanol (10:1) as an eluent
customThe eluates were evaporated in vacuo
customthe residual solid was recrystallized from ethyl acetate

Sources & evidence

ORD record: ord-d3fcd37c1fb04a1a9f81100b2f53b7e0
Source dataset: uspto-grants-1988_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04738967

Reaction notes

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