Acetamidine Hydrochloride is a compound useful in organic synthesis.
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Acetamidine hydrochloride was used in the preparation of decarboxyectoine. It was also used in the synthesis of ethyl 4-(4-hydroxyphenyl)methylidene-2-methyl-5-oxo-1-imidazolacetate.
Acetamidine hydrochloride can be used as an organic synthesis reactant for the preparation of other compounds such as 2-aminopyridine derivatives. Nucleophilic substitution and hydrolysis of 2-fluoropyridine and acetamidine hydrochloride can be used to synthesise 2-aminopyridine derivatives under catalyst-free conditions[1]. This amination reaction has the advantages of high yield, high chemoselectivity and wide substrate adaptability using acetamidine hydrochloride as the ammonia source. In addition, an efficient heterogeneous copper-catalysed cascade reaction of aryl iodides with acetamidine hydrochloride produces primary amines[2].
Acetamidine hydrochloride is an amidine salt and its conversion to 2,4,6-trimethyl-sym-triazine has been studied.
The hydrochlorde can be recrystallised from small volumes of EtOH. Alternatively it is dissolved in EtOH, filtered, Et2O is added; filter the crystalline salt off under N2 and dry it in a vacuum desiccator over H2SO4. The salt is deliquescent and should be stored in a tightly stoppered container. Its solubility in H2O is 10% at room temperature and it is soluble in Me2CO. The free base reacts strongly alkaline in H2O. It has max 224nm ( 4000) in H2O. The picrate has m 252o (sintering at ~245o). [Dox Org Synth Coll Vol I 5 1941, Davies & Parsons Chem Ind (London) 628 1958, Barnes et al. J Am Chem Soc 62 1286 1940 give m 177-178o, Beilstein 2 H 185, 2 I 85, 2 II 183, 2 III 416, 2 IV 428.]
[1] YIBIAO LI . Transition-metal-free access to 2-aminopyridine derivatives from 2-fluoropyridine and acetamidine hydrochloride1[J]. Organic & Biomolecular Chemistry, 2018, 16 41: Pages 7564-7567. DOI:10.1039/c8ob02129e.
[2] XUE HUANG. A highly efficient heterogeneous copper-catalysed cascade reaction of aryl iodides with acetamidine hydrochloride leading to primary arylamines[J]. Journal of Chemical Research-s, 2017, 46 1: 315-320. DOI:10.3184/174751917X14931195075580.
