Practical Synthesis of 3-Amino-4,5-dimethylisoxazole from 2-Methyl-2-butenenitrile and Acetohydroxamic Acid
Publication type: Journal Article
Publication date: 2007-03-01
scimago Q1
wos Q1
SJR: 0.865
CiteScore: 5.4
Impact factor: 3.5
ISSN: 10836160, 1520586X
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
3-Amino-4,5-dimethylisoxazole was prepared from technical-grade 2-methyl-2-butenenitrile and acetohydroxamic acid in a 62% overall yield on a multimole scale. The key features of this synthesis are (1) DBU treatment of the technical-grade nitrile mixture to provide a starting material of acceptable purity and (2) use of acetohydroxamic acid as an N-protected hydroxylamine equivalent. This operationally simple method provides the title compound in reasonable overall yield and free of contamination from the isomeric 5-amino-3,4-dimethylisoxazole.
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Tellew J. E., Leith L., Mathur A. Practical Synthesis of 3-Amino-4,5-dimethylisoxazole from 2-Methyl-2-butenenitrile and Acetohydroxamic Acid // Organic Process Research and Development. 2007. Vol. 11. No. 2. pp. 275-277.
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Tellew J. E., Leith L., Mathur A. Practical Synthesis of 3-Amino-4,5-dimethylisoxazole from 2-Methyl-2-butenenitrile and Acetohydroxamic Acid // Organic Process Research and Development. 2007. Vol. 11. No. 2. pp. 275-277.
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TY - JOUR
DO - 10.1021/op060239l
UR - https://doi.org/10.1021/op060239l
TI - Practical Synthesis of 3-Amino-4,5-dimethylisoxazole from 2-Methyl-2-butenenitrile and Acetohydroxamic Acid
T2 - Organic Process Research and Development
AU - Tellew, John E
AU - Leith, Leslie
AU - Mathur, Arvind
PY - 2007
DA - 2007/03/01
PB - American Chemical Society (ACS)
SP - 275-277
IS - 2
VL - 11
SN - 1083-6160
SN - 1520-586X
ER -
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@article{2007_Tellew,
author = {John E Tellew and Leslie Leith and Arvind Mathur},
title = {Practical Synthesis of 3-Amino-4,5-dimethylisoxazole from 2-Methyl-2-butenenitrile and Acetohydroxamic Acid},
journal = {Organic Process Research and Development},
year = {2007},
volume = {11},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/op060239l},
number = {2},
pages = {275--277},
doi = {10.1021/op060239l}
}
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MLA
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Tellew, John E., et al. “Practical Synthesis of 3-Amino-4,5-dimethylisoxazole from 2-Methyl-2-butenenitrile and Acetohydroxamic Acid.” Organic Process Research and Development, vol. 11, no. 2, Mar. 2007, pp. 275-277. https://doi.org/10.1021/op060239l.