Ethanol → HCID 53856373, compound

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Reaction Conditions

Reaction Steps

Ethyl (6-dimethylaminopyridazin-3-yl)carboxylate can be obtained by heating, at a temperature of about 70° C. for 4.5 hours, a suspension of 3-cyano-6-dimethylaminopyridazine (52.7 g) in a mixture of distilled water (600 cc), 10N aqueous sodium hydroxide solution (200 cc) and ethanol (400 cc). After cooling to a temperature of about 20° C., methylene chloride (200 cc) is added to the reaction mixture, which is then left to stand for 12 hours at a temperature of about 20° C. The aqueous phase is removed by decantation, acidified by addition of 12N hydrochloric acid (150 cc) and evaporated to dryness under reduced pressure. Ethanol (360 cc), 1,2-dichloroethane (360 cc) and pure methanesulphonic acid (76 g) are added to the residue thus obtained. The resulting mixture is then heated under reflux for 20 hours. After cooling to a temperature of about 20° C., the insoluble matter which has formed is filtered off and washed with methylene chloride (3 × 20 cc). A saturated aqueous sodium carbonate solution (720 cc) is added to the filtrate thus obtained. The insoluble product which forms is filtered off and washed with methylene chloride (2 × 200 cc). The aqueous phase is removed by decantation and is washed with methylene chloride (2 × 100 cc). The combined organic fractions are dried over magnesium sulphate, filtered and evaporated to dryness under reduced pressure. Ethyl (6-dimethylaminopyridazin-3-yl)carboxylate (50.81 g), melting at 112° C., is thus obtained.

Provenance & Evidence