Ethyl Acetate → 3-[(R)-2,2,1-trimethylpropylamino]-4-(2-hydroxy-6-cyanophenyl)amino-3-cyclobutene-1,2-dione

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A mixture of 3-ethoxy-4-(2-hydroxy-6-cyanophenyl)amino-3-cyclobutene-1,2-dione (0.250 g, 0.00097 mol) and (R)-2,2,1-trimethylpropylamine (0.2M in ethanol, 9.7 ml, 0.0019 mol) was stirred at room temperature for two days. TLC (2:1 ethyl acetate:hexane) indicates a loss of starting material. The reaction is evaporated on a rotary evaporator. The residue is taken up in ethyl acetate and extracted well with 0.25N HCl. The organic layer is washed once with distilled water, dried (Na2SO4), and evaporated to a solid. The solid is collected and washed with diethyl ether with several drops of ethyl acetate to give 3-[(R)-2,2,1-trimethylpropylamino]-4-(2-hydroxy-6-cyanophenyl)amino-3-cyclobutene-1,2-dione, 0.230 g (0.00073 mol, 76%)

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