1-Methylimidazole → HCID 22048491, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-methyl-1H-imidazole (0.0054 mol) in THF (10 ml) was cooled to −70° C. BuLi 1.6M (3.4 ml) was added dropwise and the mixture stood at −70° C. for 30 min. Chlorotriethylsilane (0.0054 mol) was added. The mixture was allowed to warm to 10° C. and then cooled to −70° C. BuLi 1.6M (3.4 ml) was added dropwise. The mixture stood at −70° C. for 1 hour, brought quickly to −15° C. and cooled to −70° C. THF (20 ml) and then intermediate 29) (0.0045 mol) were added. The mixture was allowed to warm to room temperature, stirred at room temperature overnight, stirred and refluxed for 24 hours, then hydrolized and extracted with DCM. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated till dryness. The residue (2.7 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 95/5/0.5; 15–40 μm). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from 2-propanone/DIPE. The precipitate was filtered off and dried, yielding 0.6 g (28%) of 4-(3-chlorophenyl)-6-[hydroxy(1-methyl-1H-imidazol-2-yl)(1-methyl-1H-imidazol-5-yl)methyl]-1-methyl-2(1H)-quinolinone, melting point 130° C.

Provenance & Evidence