Ethanol → 6-[N-(5-Chloro-2-(2-methylprop-2-en-1-yloxy)benzyl)-N-ethylamino]pyridazine-3-carboxylic acid

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Reaction Steps

A mixture of 6-[N-(5-Chloro-2-(2-methylprop-2-en-1-yloxy)benzyl)-N-ethylamino]-pyridazine-3-carboxamide (example 18) (10.5 g, 29.3 mol) and caustic liquor, 40% w/v (10 ml, 100 mmol) in ethanol (150 ml) was stirred at reflux for 16 hours. The solvent was evaporated at reduced pressure and the residue partitioned between 2N hydrochloric acid (70 ml) and dichloromethane (200 ml). The organic layer was dried over anhydrous magnesium sulphate, filtered and evaporated to give a brown gum (10.0 g), which was redissolved in ether (200 ml) and allowed to crystallise slowly over 12 hours to give the title compound as a pale yellow solid (4.6 g, 45%) m.p. 130-131° C.

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