Amide Hydrolysis Reaction Using tert-Butyl Nitrite

doi:10.6023/cjoc202310004

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (2): 550-560.DOI: 10.6023/cjoc202310004 Previous Articles Next Articles

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亚硝酸叔丁酯参与的酰胺水解反应

陶苏艳, 项紫欣, 白俊杰, 万潇, 万小兵^*()

苏州大学材料与化学化工学部江苏省有机合成重点实验室江苏苏州 215123

收稿日期:2023-10-07 修回日期:2023-11-02 发布日期:2023-11-07
基金资助:
国家自然科学基金(21973068); 国家自然科学基金(21971175)

Amide Hydrolysis Reaction Using tert-Butyl Nitrite

Suyan Tao, Zixin Xiang, Junjie Bai, Xiao Wan, Xiaobing Wan()

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, Jiangsu 215123

Received:2023-10-07 Revised:2023-11-02 Published:2023-11-07
Contact: * E-mail: wanxb@suda.edu.cn
Supported by:
National Natural Science Foundation of China(21973068); National Natural Science Foundation of China(21971175)

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Abstract

Amide is a compound that serves important functions and acts as versatile synthons, finding wide applications in organic synthesis and pharmaceutical chemistry. In this study, the mild hydrolysis reaction of primary amides using tert-butyl nitrite is showed, which leads to the formation of diverse carboxylic acids. This method stands out because it operates under neutral conditions, has a wide range of applicable substrates, and is compatible with various functional groups.

Key words: amide, carboxylic acids, tert-butyl nitrite, hydrolysis reaction

Cite this article

Suyan Tao, Zixin Xiang, Junjie Bai, Xiao Wan, Xiaobing Wan. Amide Hydrolysis Reaction Using tert-Butyl Nitrite[J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 550-560.

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References 26

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Entry^a	Solvent	Yield^b/%
1	Acetone	n.d.
2	DMF	n.d.
3	DMSO	Trace
4	DCM	38
5	THF	22
6	CH₃CN	90
7	EA	58
8	CH₃OH	n.d.
9	Toluene	58
10	Cyclohexane	36
11	H₂O	17
12^c	CH₃CN	76
13^d	CH₃CN	72
14^e	CH₃CN	43
15^f	CH₃CN	86
16^g	CH₃CN	84

Entry^a	Solvent	Yield^b/%
1	Acetone	n.d.
2	DMF	n.d.
3	DMSO	Trace
4	DCM	38
5	THF	22
6	CH₃CN	90
7	EA	58
8	CH₃OH	n.d.
9	Toluene	58
10	Cyclohexane	36
11	H₂O	17
12^c	CH₃CN	76
13^d	CH₃CN	72
14^e	CH₃CN	43
15^f	CH₃CN	86
16^g	CH₃CN	84

Entry^a	Condition	Yield^b/%
1	—	90
2	ⁱPrONO instead of ^tBuONO	Trace
3	ⁱBuONO instead of ^tBuONO	72
4	ⁿBuONO instead of ^tBuONO	77
5	ⁱAmONO instead of ^tBuONO	85
6	O₂	89
7	N₂	78
8	At room temperate	66

Entry^a	Condition	Yield^b/%
1	—	90
2	ⁱPrONO instead of ^tBuONO	Trace
3	ⁱBuONO instead of ^tBuONO	72
4	ⁿBuONO instead of ^tBuONO	77
5	ⁱAmONO instead of ^tBuONO	85
6	O₂	89
7	N₂	78
8	At room temperate	66

亚硝酸叔丁酯参与的酰胺水解反应

Amide Hydrolysis Reaction Using tert-Butyl Nitrite

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