Even though this latter method failed to produce 2, the ease of formation of 4 from 3 indicated that the nitrile functionality of 3 was capable of reacting with nucleophiles and that the failure of ammonia to convert 3 into 2 was due to the diminished nucleophilicity of ammonia (relative to hydroxylamine). To overcome this problem, acidic conditions were used to enhance the electrophilicity of the
