Sodium hydride → HCID 136342844, compound

Participants

Reaction Steps

To a round-bottomed flask containing 4-chloro-1-(3-chloropropyl)-1H-imidazo[4,5-c]quinolin-2-amine (7.92 g, 26.8 mmol) was added N,N-dimethylacetamide (200 mL) and the mixture was stirred for 5 minutes. To the stirred solution was added sodium hydride (60% dispersion in mineral oil, 3.9 g, 80.54 mmol) and the reaction was stirred at 50° C. After 1.5 h the reaction was cooled to ambient and quenched by the careful addition of water (1 L). The reaction was transferred to a separatory funnel and ethyl acetate (1 L) was added. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (1 L). The organic layers were combined, washed with water (2×1 L), dried (MgSO4), filtered, and the solvent was evaporated. The resultant product was dried under reduced pressure to afford 6-chloro-8,9,10,11-tetrahydropyrimido[1′,2′:1,2]imidazo[4,5-c]quinoline (6.54 g).

Provenance & Evidence