The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Reduction of Formisobutyraldol and Its Oxime》. Authors are Boehm, Rudolf.The article about the compound:2-Cyano-2-methylpropanoic acidcas:22426-30-8,SMILESS:CC(C)(C#N)C(O)=O).Reference of 2-Cyano-2-methylpropanoic acid. Through the article, more information about this compound (cas:22426-30-8) is conveyed.
Dry distillation of formisobutyr aldoloxime yields water and an oily layer containing nitrile and anhydride. These were separated by distillation in vacuum; anhydride b24, 65°, nitrile b24 120°. Nitrile of α-dimethylhydracrylic acid, b11 97°, is a colorless liquid, faint garlic odor, which turns brown in air. Saponification yields hydroxypivalinic acid. Anhydride, b. 137°, Yields formisobutyraldol and hydroxylamine on hydrolysis, reacts readily with sodium, forms an ester with acetic anhydride, b. 103°. Attempts to make the nitrile from the oxime by acetic anhydride gave the acetic ester of the nitrile, which has an agreeable, slightly garlic odor, b13, 91.5°, and analysis agrees with C7H11NO2. α-Cyanisobutyric acid, m, 56°-57°, obtained by oxidation of the acetic ester of nitrile with dilute permanganate. Oxidation of the nitrile obtained by distilling formisobutyraldoloxime yields α-cyanisobutyric acid and much isobutyric acid unless oxidation is carried out at low temperature. Reduction of formisobutyraldol with sodium amalgam gave the a 2-dimethylpropane-1,3-diol. With zinc and hydrochloric acid different products were obtained under different conditions. With all zinc and acid added at once to the aqueous solutions of aldol and kept cool two crystalline products and an oil formed. Oil alone formed if acid was added gradually to zinc and aldol. The two crystalline products melted at 137.5° and 63.5°, respectively. The amount of the former was increased by carrying on the reduction at higher temperature. Analyses indicate that both compounds are formed by loss of water from two molecules of aldol, like hydrobenzoin. Structural formula still uncertain. Electrolytic reduction with lead cathode and carbon anode, 2 amp. per sq. dm., gave the oily reduction product, with 5 amp. both crystalline products and the oily one.
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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method