Synthesis of 4-amino-3,5-dinitro-1H-pyrazole using vicarious nucleophilic substitution of hydrogen

Citation
Rd. Schmidt et al., Synthesis of 4-amino-3,5-dinitro-1H-pyrazole using vicarious nucleophilic substitution of hydrogen, J HETERO CH, 38(5), 2001, pp. 1227-1230
Citations number
17
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
JOURNAL OF HETEROCYCLIC CHEMISTRY
ISSN journal
0022152X → ACNP
Volume
38
Issue
5
Year of publication
2001
Pages
1227 - 1230
Database
ISI
SICI code
0022-152X(200109/10)38:5<1227:SO4UVN>2.0.ZU;2-R
Abstract
A novel synthesis of the title compound was achieved by direct amination us ing Vicarious Nucleophilic Substitution (VNS) methodology. Reaction of 1,1, 1-trimethylhydrazinium iodide with 3,5-dinitropyrazole in DMSO produces 4-a mino-3,5-dinitro-1H-pyrazole as a 1:1 crystal solvate with DMSO. Recrystall ization from water yields the monohydrated crystal. Recrystallization of th e monohydrate from butyl acetate yields the compound in pure form.