The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Methyl β-(m-chloroanilino)acrylate》. Authors are Gray, F. W.; Mosher, Harry S.; Whitmore, F. C.; Oakwood, T. S..The article about the compound:Ethyl 3-Ethoxy-2-Propenoatecas:1001-26-9,SMILESS:O=C(OCC)/C=C/OCC).COA of Formula: C7H12O3. Through the article, more information about this compound (cas:1001-26-9) is conveyed.
HCCCO2Me (9.5 g.) and 9.0 g. m-ClC6H4NH2 (I) stirred 70 hrs. at 25-30°, and the mixture chilled and filtered yielded 11.2 g. Me β-(m-chloroanilino)acrylate (II), colorless needles from MeOH, m. 148-50° (m.p. greatly dependent on rate of heating), cyclized to 4-hydroxy-7-chloroquinoline (IIA) (Price, et al. (C.A. 40, 5741.1)). I.HCl (19.8 g.) in 150 cc. water at 10° treated with 17.7 g. (MeO)2CHCH2CO2Me, and the mixture warmed to 25° after 15 min. and stirred overnight yielded 24 g. material (III), m. 123-6° (from MeOH), analyzing correctly for II, but attempted cyclization by heating 2 g. with Ph2O gave only a small amount (0.15 g.) of 1,3-bis(m-chlorophenylurea) (IV), m. 248°. I (5.1 g.) and 4.5 g. MeOCH:CHCO2Me heated 1 hr. at 100° and 740 mm., then 1 hr. at 50° and 15 mm., the solution added dropwise to 150 cc. boiling Ph2O, the mixture refluxed 1 hr., cooled, left at room temperature 4 hrs., and filtered yielded 2 g. IV, white, crystalline needles from MeOH, m. 250°. EtOCH:CHCO2Et (7.6 g.) and 6.8 g. I yielded 1.3 g. IV, m. 250°. This method for preparing IIA offers another method for synthesizing antimalarials of the chloroquine type.
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Reference:
Bromide – Wikipedia,
bromide – Wiktionary