Study of 1-Methyl-3-propyl-4-aminopyrazole-5-carbonitrile

Min Xu; Daxin Shi; Mingxing Liu; Qi Zhang; Jiarong Li

doi:10.6023/cjoc201512042

Study of 1-Methyl-3-propyl-4-aminopyrazole-5-carbonitrile

Min Xu, Daxin Shi, Mingxing Liu, Qi Zhang, Jiarong Li^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Beijing Institute of Technology

Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)

Abstract

1-Methyl-3-propyl-4-aminopyrazole-5-carbonitrile was synthesized by using 1-methyl-3-propylpyrazole-5-formic as starting materials in four steps reaction including acylation, dehydration, nitrification and reduction. Then pyrazolopyrimidinone derivatives were obtained from the condensation of 1-methyl-3-propyl-4-aminopyrazole-5-carbonitrile and aldehydes. 1-Methyl-3-propyl-4-nitropyrazole-5-carbonitrile was reduced to amine in the presence of palladium-charcoal. Three intermediate products, hydroxylamine, azoxypyrazole and azopyrazole, were separated and detected with HPLC and HPLC-HRMS during the formation of amine pyrazole. Possible reduction mechanism was proposed. The structures of products were characterized by ¹H NMR, ¹³C NMR, IR spectra and MS.

Original language	English
Pages (from-to)	1611-1616
Number of pages	6
Journal	Chinese Journal of Organic Chemistry
Volume	36
Issue number	7
DOIs	https://doi.org/10.6023/cjoc201512042
Publication status	Published - 1 Jul 2016

Keywords

1-methyl-3-propyl-4-aminopyrazole-5-carbonitrile
Pyrazolopyrimidinone derivative
Reduction mechanism

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title = "Study of 1-Methyl-3-propyl-4-aminopyrazole-5-carbonitrile",

abstract = "1-Methyl-3-propyl-4-aminopyrazole-5-carbonitrile was synthesized by using 1-methyl-3-propylpyrazole-5-formic as starting materials in four steps reaction including acylation, dehydration, nitrification and reduction. Then pyrazolopyrimidinone derivatives were obtained from the condensation of 1-methyl-3-propyl-4-aminopyrazole-5-carbonitrile and aldehydes. 1-Methyl-3-propyl-4-nitropyrazole-5-carbonitrile was reduced to amine in the presence of palladium-charcoal. Three intermediate products, hydroxylamine, azoxypyrazole and azopyrazole, were separated and detected with HPLC and HPLC-HRMS during the formation of amine pyrazole. Possible reduction mechanism was proposed. The structures of products were characterized by 1H NMR, 13C NMR, IR spectra and MS.",

keywords = "1-methyl-3-propyl-4-aminopyrazole-5-carbonitrile, Pyrazolopyrimidinone derivative, Reduction mechanism",

author = "Min Xu and Daxin Shi and Mingxing Liu and Qi Zhang and Jiarong Li",

note = "Publisher Copyright: {\textcopyright} 2016 Chinese Chemical Society & SIOC, CAS.",

year = "2016",

month = jul,

day = "1",

doi = "10.6023/cjoc201512042",

language = "English",

volume = "36",

pages = "1611--1616",

journal = "Chinese Journal of Organic Chemistry",

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TY - JOUR

T1 - Study of 1-Methyl-3-propyl-4-aminopyrazole-5-carbonitrile

AU - Xu, Min

AU - Shi, Daxin

AU - Liu, Mingxing

AU - Zhang, Qi

AU - Li, Jiarong

PY - 2016/7/1

Y1 - 2016/7/1

N2 - 1-Methyl-3-propyl-4-aminopyrazole-5-carbonitrile was synthesized by using 1-methyl-3-propylpyrazole-5-formic as starting materials in four steps reaction including acylation, dehydration, nitrification and reduction. Then pyrazolopyrimidinone derivatives were obtained from the condensation of 1-methyl-3-propyl-4-aminopyrazole-5-carbonitrile and aldehydes. 1-Methyl-3-propyl-4-nitropyrazole-5-carbonitrile was reduced to amine in the presence of palladium-charcoal. Three intermediate products, hydroxylamine, azoxypyrazole and azopyrazole, were separated and detected with HPLC and HPLC-HRMS during the formation of amine pyrazole. Possible reduction mechanism was proposed. The structures of products were characterized by 1H NMR, 13C NMR, IR spectra and MS.

AB - 1-Methyl-3-propyl-4-aminopyrazole-5-carbonitrile was synthesized by using 1-methyl-3-propylpyrazole-5-formic as starting materials in four steps reaction including acylation, dehydration, nitrification and reduction. Then pyrazolopyrimidinone derivatives were obtained from the condensation of 1-methyl-3-propyl-4-aminopyrazole-5-carbonitrile and aldehydes. 1-Methyl-3-propyl-4-nitropyrazole-5-carbonitrile was reduced to amine in the presence of palladium-charcoal. Three intermediate products, hydroxylamine, azoxypyrazole and azopyrazole, were separated and detected with HPLC and HPLC-HRMS during the formation of amine pyrazole. Possible reduction mechanism was proposed. The structures of products were characterized by 1H NMR, 13C NMR, IR spectra and MS.

KW - 1-methyl-3-propyl-4-aminopyrazole-5-carbonitrile

KW - Pyrazolopyrimidinone derivative

KW - Reduction mechanism

UR - http://www.scopus.com/inward/record.url?scp=84982918543&partnerID=8YFLogxK

U2 - 10.6023/cjoc201512042

DO - 10.6023/cjoc201512042

M3 - Article

AN - SCOPUS:84982918543

SN - 0253-2786

VL - 36

SP - 1611

EP - 1616

JO - Chinese Journal of Organic Chemistry

JF - Chinese Journal of Organic Chemistry

IS - 7

ER -

Study of 1-Methyl-3-propyl-4-aminopyrazole-5-carbonitrile

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Keywords

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