The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Alkylcyanoacetic acids》. Authors are Hessler, John C..The article about the compound:2-Cyano-2-methylpropanoic acidcas:22426-30-8,SMILESS:CC(C)(C#N)C(O)=O).Computed Properties of C5H7NO2. Through the article, more information about this compound (cas:22426-30-8) is conveyed.
α-Methyl-α-cycanopropionic acid, obtained in 2.5 g. yield from 8.7 g. of the Et ester allowed to stand overnight in running H2o with 9 g. KOH in 100 cc. MeOH, b12 132-5 °, m. 57°; silver. salt; barium salt, prisms with 18 mols. H2O. Et2C(CN)CO2H, in 31 g-yield from 42.5, g. of the ester and 28 g. KOH in 300 cc. MeOH, m. 61° (Hesse, Am.Chem. J. 18, 746(1896), gives 57°). Salts: silver, bulky precipitate; barium, needles; lead, flat flakes; calcium, needles with 3 H2O; strontium, prisms with 3 H2O; cadmium, flat plates with 3 H2O; copper, bright green rectangles with 3 H2O. From 50 g. NCCH2. CO2Et, in 100 cc. alc. and 10.2 g. Na in 250 cc. alc. treated with 80 g. PrI and allowed to stand overnight, is obtained 51.5 g. crude product (a), b24 117-30°; this is shaken in Et2O with 10% NaOH and the alk. extract acidified with dilute H2SO4 and extracted with Et2O, giving 24.9 g. α-cyanovaleric acid; silver and barium salts; Et ester, from the Ag salt and EtI, b755 218-9°, d32 0.972. The Et2O solution of (a), after extraction with NaOH, yields 17.8 g. of Et α-propyl-α-cyanovalerate, b22-3 129-32°, d26 0.93; free acid, rhombic prisms, m. 41°, becoming syrupy over H2SO4 in vacuo; after 5 days it contained 1 mol. H2O; silver salt, seps. with 1 H2O. In the same way from 50 g. NCCH2CO2Et are obtained 20.5 g. γ-methyl-α-cyanovaleric acid (silver salt, powder; barium salt, needles with 2 H2O; Et ester, b755 223-4°, d35 0.958), and 28. 1 g. Et γ-methyl-α-isobutyl-α-cyanovalerate, b755 245-50°, d31 0.915 (free acid, m. 82°; silver salt, bulky precipitate). Copper δ-methyl-α-cyanocaproate (cf. C. A. 7, 3506), blue crystalline precipitate with 7 H2O, turning green in vacuo over H2SO4; barium salt, needles with 2 H2O; chloride, liquid; anilide, needles, m. 102°. δ-Methyl-α-isoamyl-α-cyanocaproic acid, from the ester and KOH in MeOH,needles from C6H6, m. 74-5°; ammonium salt, flakes, 2.9 g. of which dissolve in 100 cc. H2O at 16°; silver salt, precipitate; copper salt, green flakes with 3 H2O; calcium salt, rhomboids with 4 H2O; amide, needles from alc., m. 152°. Lead benzylcyanoacetate, bulky crystalline precipitate with 3 H2O; calcium and barium salts, needles with 3 and 6 H2O; copper salt, deep blué precipitate with 5 H2O which it loses at 65°, turning green, m. 105-15° (decomposition); chloride, slightly colored liquid, does not distil under 35 mm. at a bath temperature of 290°. (PhCH2)2-(CN)CO2H, m. 194-5° (Cassirer, Ber. 25, 3027(1892), gives 188-9°); silver salt, precipitate; copper salt, blue precipitate with 1 H2O, turning green on drying. The Me ester, 6-sided plates from Et2O-ligroin, m. 78-9°, is obtained in 4.9 g. yield, together with 1.6 g. of the acid, when 20 g. NCCH2CO2Et in 125 cc. MeOH and 4.07 g. Na in 125 cc. MeOH are allowed to stand with 22 g. PhCH2Cl 14 h. and the fraction b15 195-260° of theproduct is shaken in Et2O with 10% NaOH.
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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method