The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Improved synthesis of 3-methylpyrrole》. Authors are Lancaster, Roscoe E. Jr.; VanderWerf, Calvin A..The article about the compound:3-Methyl-1H-pyrrolecas:616-43-3,SMILESS:CC1=CNC=C1).Name: 3-Methyl-1H-pyrrole. Through the article, more information about this compound (cas:616-43-3) is conveyed.
Pure 3-methylpyrrole (I) was synthesized in 37.8% yield starting with K phthalimide (II) by condensation of aminoacetone (III) with di-Et oxalacetate (IV) and subsequent hydrolysis and decarboxylation of the product, 2-carboxy-3-carbethoxy-4-methylpyrrole (V). The chief improvement is the method for in situ synthesis of III and in the improvement of the subsequent steps as well as the more complete characterization of I. II (250 g.) with 200 g. ClCH2Ac heated gently until reaction started, the reaction allowed to go to completion at room temperature, and the product isolated gave 269 g. N-acetonylphthalimide (VI), m. 116.0-16.8° (H2O). Concentrated HCl (150 ml.) and 75 ml. H2O refluxed 4 hrs. with 50 g. crude VI, cooled, the pH brought to 1.5, the filtrate slowly added to 45 g. IV Na salt in 400 ml. H2O while the temperature was maintained at 75° and the pH at 5 with small additions of NaOH solution, the mixture cooled, the precipitate removed, the pH of the filtrate adjusted to 8, the solution heated 0.5 hr. at 75°, reacidified, and separated gave 25.5 g. V, m. 195.7-6.8°. V (67 g.) refluxed 24 hrs. with 440 g. KOH in 1250 ml. H2O, the pH adjusted to 9, cooled, and collected gave after acidification of the filtrate 42.5 g. 3-carbethoxy-4-methylpyrrole (VII), m. 152.6-3.7°. VII (22 g.) on dry distillation gave 10.6 g. I, b740 142-3°, n20D 1.4970, n25D 1.4949. The absorption bands in the infrared spectra of I and 2-methylpyrrole (II) were compared in a table and the infrared spectra of 12.25% solutions of I and II in CHCl3 taken and the curves shown in figures.
The article 《Improved synthesis of 3-methylpyrrole》 also mentions many details about this compound(616-43-3)Name: 3-Methyl-1H-pyrrole, you can pay attention to it, because details determine success or failure
Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate