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Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 01: 145 - 148

DOI: https://doi.org/10.6023/cjoc1108121

Articles

Synthesis of Isotope-Labeled 15N-N,N-Dimethylaniline

  • YANG Wei-Cheng ,
  • QI Qing-Rui ,
  • LIU Wei-Xia ,
  • LI Mei-Hua ,
  • LUO Yong
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  • a Research & Development Center, Shanghai Research Institute of Chemical Industry, Shanghai 200062;
    b Branch of Professional Education, Xinjiang Normal University, Urumqi 830046

Received date: 2011-08-12

  Revised date: 2011-09-15

  Online published: 2011-09-30

Supported by

Project supported by the Special Funds for System-Transformed Institutes of Science and Technology Ministry (No. 2011EG116066) and the Special Funds of the General Administration of Quality Supervision, Inspection and Quarantine (No. 2009IK134).

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Abstract

An efficient synthesis of 15N-N,N-dimethylaniline with 15NH4Cl as the common substrate is reported. Ammoniation of benzoyl chloride with 15NH4Cl provided 15N-benzamide, which was converted to 15N-aniline by Hofmann degradation. Methylation of 15N-aniline with methyl p-toluenesulfonate provided 15N-N,N-dimethylaniline. The overall yield of 15N-N,N-dimethylaniline in three steps was 58.3% based on 15NH4Cl consumed. As-synthesized product was shown by IR, NMR, HPLC and MS to be target compound. Its chemical purity is higher than 99.0% and isotopic enrichment is higher than 98.4% 15N.

Key words： isotope-labeled; synthesis; N,N-dimethylaniline; characterization; methylation

Cite this article

YANG Wei-Cheng , QI Qing-Rui , LIU Wei-Xia , LI Mei-Hua , LUO Yong . Synthesis of Isotope-Labeled 15N-N,N-Dimethylaniline[J]. Chinese Journal of Organic Chemistry, 2012 , 32(01) : 145 -148 . DOI: 10.6023/cjoc1108121

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