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Purification method of O-benzylhydroxylamine hydrochloride

A technology of hydroxylamine hydrochloride and purification method, which is applied in the field of organic synthesis, and can solve the problems of not mentioning the purity of the target substance, not giving CNMR data and IR data, etc.

Inactive Publication Date: 2015-09-23
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In the structural characterization of the Bonaccorsi method, only the product O-(benzyl) hydroxylamine hydrochloride 1 HNMR data, not given its 13 CNMR data and IR data, also did not mention the purity of the target

Method used

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  • Purification method of O-benzylhydroxylamine hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Add 19ml of absolute ethanol to the three-necked flask, add 2.7g of crude O-(benzyl)hydroxylamine hydrochloride under stirring at 25°C, and heat up to 80°C, the solid is completely dissolved, and react for 1h. The reaction solution was cooled to -5°C, and white flaky crystals precipitated out of the solution. The solid was collected by filtration and dried to obtain 2.16 g of O-(benzyl) hydroxylamine hydrochloride, with a yield of 80%, a purity of 99%, and m.p.237-238°C.

[0018] Structure Identification

[0019] 1H NMR (300MHz, DMSO-d6,): δ5.05 (2H, s), 7.40 (5H, s), 11.25 (3H, broad s);

[0020] 13C NMR (300MHz, DMSO-d6,): δ 133.7, 129.1, 128.6, 75.7, 39.5.

[0021] IR(KBr):3309,3033,2921,1683,1591,1494,1454,1362,1188,1079,999,918,848,822,744,703,611,483cm-l

[0022] The above structure identification data prove that the compound obtained by this method is indeed the target O-(benzyl)hydroxylamine hydrochloride.

Embodiment 2

[0024] Add 21ml of absolute ethanol to the three-necked flask, add 2.7g of crude O-(benzyl)hydroxylamine hydrochloride under stirring at 25°C, and heat up to 80°C, the solid dissolves completely and reacts for 1 hour. The reaction solution was cooled to -5°C, and white flaky crystals precipitated out of the solution. The solid was collected by filtration and dried to obtain 2.04 g of O-(benzyl) hydroxylamine hydrochloride with a yield of 75.6% and a purity of 99%.

Embodiment 3

[0026] Add 19ml of absolute ethanol to the three-necked flask, add 2.7g of crude O-(benzyl)hydroxylamine hydrochloride under stirring at 25°C, and heat up to 80°C, the solid is completely dissolved, and react for 1h. The reaction solution was cooled to 0°C, and white flaky crystals precipitated out of the solution. The solid was collected by filtration and dried to obtain 1.98 g of O-(benzyl) hydroxylamine hydrochloride, with a yield of 73.3% and a purity of 98.9%.

[0027] Application of O-(benzyl) hydroxylamine hydrochloride purified by the inventive method

[0028] N,N',N"-trihydroxyisocyanic acid (THICA) is an efficient free radical catalyst. THICA often catalyzes alkylaromatics containing strong charge-absorbing groups such as nitrotoluene together with metal or non-metallic initiators. Oxidation into the corresponding acid, due to the use of green oxidant oxygen in the catalytic oxidation of THICA, and the conversion rate of the substrate is high, the post-treatment is ...

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Abstract

The invention provides a purification method of O-benzylhydroxylamine hydrochloride. The method includes the following steps of dissolving a crude product of the O-benzylhydroxylamine hydrochloride in absolute ethyl alcohol during stirring at a temperature of 20 DEG C to 30 DEG C, completely dissolving the solid after the temperature is raised to 80 DEG C, reacting for 0.5 h to 1.5 h under backflow, cooling reaction liquid to a temperature of -5 DEG C to 0 DEG C, separating out white tabular crystal from a solution, filtering out and collecting the solid, and conducting drying to obtain the O-benzylhydroxylamine hydrochloride, wherein the ratio of the mass of the crude product of the O-benzylhydroxylamine hydrochloride to the volume of the absolute ethyl alcohol is 1g to 7-9 ml. The method is used for purifying the crude product of the O-benzylhydroxylamine hydrochloride so that the high-purity O-benzylhydroxylamine hydrochloride can be obtained.

Description

technical field [0001] The invention relates to a purification method of O-(benzyl) hydroxylamine hydrochloride, which belongs to the field of organic synthesis. Background technique [0002] O-(benzyl)hydroxylamine hydrochloride is a commonly used intermediate in industry, and it is widely used in organic synthesis. It has a melting point of 238°C and a boiling point of 253.9°C. It can be used in ketone derivatization reactions in gas phase analysis, and can also be used to synthesize compounds such as hydroxylamine, N-hydroxypeptide and R-hydroxybenzylamine. Among them, the compound hydroxamate synthesized with O-(benzyl)hydroxylamine hydrochloride as a substrate is a commonly used inhibitor of an effective angiotensin-converting enzyme (ACE), and O-(benzyl)hydroxylamine salt The α-lactam antibiotics synthesized with acid salts as intermediates have been widely used in the pharmaceutical industry. [0003] The traditional method of preparing O-(benzyl)hydroxylamine hydro...

Claims

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Application Information

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IPC IPC(8): C07C239/20C07D251/34
Inventor 陆婷婷姬月萍张丽洁刘亚静丁峰汪伟朱勇葛忠学汪营磊卢先明高福磊刘卫孝陈斌莫洪昌
Owner XIAN MODERN CHEM RES INST
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