Ammonium Salt-Accelerated Hydrazinolysis of Unactivated Amides

Mechanistic Investigation and Application to a Microwave Flow Process

Megumi Noshita, Yuhei Shimizu, Hiroyuki Morimoto, Shuji Akai, Yoshitaka Hamashima, Noriyuki Ohneda, Hiromichi Odajima, Takashi Ohshima

Research output: Contribution to journalArticle

Abstract

A study of ammonium salt-accelerated hydrazinolysis of unactivated amides is described. We first studied the reaction mechanism by kinetic experiments and DFT calculations and found that cooperation of the hydrazinium salt and hydrazine is important for promoting the cleavage of unactivated amides. Next, we applied the reaction to a microwave flow process, and the amine products were isolated on a multigram scale.

Original languageEnglish
Pages (from-to)588-594
Number of pages7
JournalOrganic Process Research and Development
Volume23
Issue number4
DOIs
Publication statusPublished - Apr 19 2019

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hydrazine
Ammonium Compounds
Amides
amides
Salts
Microwaves
salts
microwaves
hydrazines
Discrete Fourier transforms
Amines
cleavage
amines
Kinetics
kinetics
products
Experiments
hydrazinium

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Ammonium Salt-Accelerated Hydrazinolysis of Unactivated Amides : Mechanistic Investigation and Application to a Microwave Flow Process. / Noshita, Megumi; Shimizu, Yuhei; Morimoto, Hiroyuki; Akai, Shuji; Hamashima, Yoshitaka; Ohneda, Noriyuki; Odajima, Hiromichi; Ohshima, Takashi.

In: Organic Process Research and Development, Vol. 23, No. 4, 19.04.2019, p. 588-594.

Research output: Contribution to journalArticle

Noshita, Megumi ; Shimizu, Yuhei ; Morimoto, Hiroyuki ; Akai, Shuji ; Hamashima, Yoshitaka ; Ohneda, Noriyuki ; Odajima, Hiromichi ; Ohshima, Takashi. / Ammonium Salt-Accelerated Hydrazinolysis of Unactivated Amides : Mechanistic Investigation and Application to a Microwave Flow Process. In: Organic Process Research and Development. 2019 ; Vol. 23, No. 4. pp. 588-594.
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