The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Ring-chain tautomerism in the reaction products of aminophenol and some ethoxymethyleneacetates》. Authors are Nozoe, Tetsuo; Doi, Kozo.The article about the compound:Ethyl 3-Ethoxy-2-Propenoatecas:1001-26-9,SMILESS:O=C(OCC)/C=C/OCC).Application of 1001-26-9. Through the article, more information about this compound (cas:1001-26-9) is conveyed.
o-Aminophenol (I) (1.1 g.) and 2.2 g. di-Et (ethoxymethylene)malonate was heated at 130° 30 min. and crystallized to give quant. yield of 2-(ω,ω-diethoxyearbonylmethyl)benzoxazoline (II), prisms, m. 1401° (EtOH). II did not show coloration with alc. FeCl3 and was inert to the action of CH2N2. II (5.6 g.) was pyrolyzed at 250° and fractions b. 175-185° (A) (1.6 g.) and 195-9° (B) (2.7 g.) were collected. Redistillation of A gave benzoxazole (III), b. 180-2°, m. 30-1°; B was identified as di-Et malonate. Similar condensation of I with Et (ethoxymethylene)acetoacetate and di-Et (ethoxymethylene)cyanoacetate gave, resp., 2-(ω-acetyl-ω-ethoxycarbonylmethyl)benzoxazoline (IV), prisms, m. 146-7° (MeOH), and 2(ω-ethoxycarbonyhnethyl-ω-cyanomethyl)benzoxazoline (V), needles, m. 191-2° (MeOH). Pyrolysis of IV gave Et acetoacetate and III, and V similarly gave Et cyanoacetate and III.
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Reference:
Bromide – Wikipedia,
bromide – Wiktionary