Sodium Hydroxide → 1-Butoxy-2-(3-bromopropylamino)-1-cyclobutene-3,4-dione

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Reaction Steps

Solid 3-bromopropylamine hydrobromide (31.0 g, 0.1416 mole) was added with stirring to a solution of sodium hydroxide (5.77 g, 0.140 mole) in methanol (152 mL) and stirred at ambient temperature for 15 minutes. The solution was cooled to 0°-5° C. and then added with stirring to the solution of Step A. The mixture was stirred at 22° C. for 1.5 hours then concentrated under reduced pressure (40° C.) to about 120 mL volume. Toluene (120 mL) was added and the mixture was washed with water (240 mL). The organic layer was dried (sodium sulfate), filtered, and the solvent was evaporated under reduced pressure to give 38.64 g (95.0 % yield) of the title compound as an off-white solid. The product was used without further purification in the subsequent reaction.

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