Sodium Hydroxide → 6-[N-(5-Bromo-2-(2-methylpropoxy)benzyl)-N-ethylamino]pyridazine-3-carboxylic Acid

Participants

Reaction Steps

Butyl 6-[N-(5-bromo-2-(2-methylpropoxy)benzyl)-N-ethylamino]pyridazine-3-carboxylate (reference example 10) (0.22 g, 0.47 mmol) in THF (3 ml) and methanol (3 ml) was treated with a 1N solution of aqueous sodium hydroxide (3 ml) and left at ambient temperature for 1.5 hours (after which time TLC (1:1 diethyl ether/hexane) indicated that none of the ester remained). The reaction mixture was evaporated to low bulk, taken up in a little water and acidified with acetic acid to produce a gum. The gum did not solidify so it was extracted with ethyl acetate (×2) and the combined extracts washed with brine, dried (MgSO4) and evaporated to give a gum. The gum was evaporated from toluene and dichloromethane to give the title compound as a foam (140mg, 73%).

Provenance & Evidence