The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《On cyclic intermediates in substitution reactions. VII. The alkaline solvolysis of some N-aryl-4-bromobutanamides》. Authors are Heine, Harold W.; Love, Peter; Bove, John L..The article about the compound:1-(4-Chlorophenyl)pyrrolidin-2-onecas:7661-33-8,SMILESS:O=C1N(C2=CC=C(Cl)C=C2)CCC1).Product Details of 7661-33-8. Through the article, more information about this compound (cas:7661-33-8) is conveyed.
cf. C.A. 49, 1556b. The rates of the solvolysis of 3 N-aryl-4-bromobutanamides have been studied in MeOH. The rates of the reaction as determined by the measurement of the release of bromide ion are 1st order with respect to MeO-. The reaction products are the corresponding pyrrolidones. These results are discussed in terms of a mechanism involving the formation and conversion of a bromoamido ion to a pyrrolidone. SOCl2 (20 cc.) added dropwise to 37.1 g. Br(CH2)3CO2H, the mixture held 2 days at room temperature, the excess SOCl2 removed in vacuo, and the residue distilled gave a distillate, b31 88-90°, nD201.4899; a 37.1-g. sample of the distillate added dropwise with stirring to 37.2 g. PhNH2 in 500 cc. CHCl3, the mixture stirred 15 min., the precipitate filtered and washed with CHCl3, the combined filtrate and washing concentrated in vacuo, and the crude residue dissolved in ligroine, b. 65-110°, cooled, and then chilled to -78° gave 38% Br(CH2)3CONHPH (I), m. 75-6°. In the same manner except with a reaction time of 4 hrs. was prepared the p-Me derivative (II) of I, m. 90-1° (from petr. ether), in 63.2% yield. The p-Cl derivative (III) of I, m. 100-1° (from petr. ether), was prepared with a reaction time of 2 hrs. in 69.2% yield. A solution (100 cc.) 0.05M in NaOMe and 0.05M in III kept at 22.9° until all bromide ion had been released, the MeOH evaporated in vacuo, the residue washed with H2O, and the residue dried at 50° and recrystallized from petr. ether (b. 30-60°) gave 0.940 g. 1-(p-chlorophenyl)pyrrolidone (IV), m. 95-7°. The average rate constants of the alk. solvolyses determined at 22.90° were: III 5.65, I 1.80, and II 1.03 × 10 l./min./mole.
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