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Process for producing N-benzyl hydroxylamine and hydrochlorate

A technology of benzylhydroxylamine and hydrochloride, applied in the field of preparation of N-benzylhydroxylamine and hydrochloride thereof, can solve the problems such as no good improvement, low yield, complicated process, etc., and achieves mild reaction , low price, simple conditions

Active Publication Date: 2009-05-13
江西豫章药业有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The yield of the former is not high, while the process of the latter is complicated and the cost is high
Domestic technology in this area has not been improved very well, and there is no complete synthesis from the most easily available raw material benzaldehyde

Method used

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  • Process for producing N-benzyl hydroxylamine and hydrochlorate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] 1. Oximation

[0013] In a 1-liter clean four-neck flask, add 600 ml of water, 72 g (1.02 moles) of hydroxylamine hydrochloride, stir and dissolve, add 165 g of 25% NaOH solution, and cool the ice water to about 20°C, between 20-30°C 108 g (1.02 mol) of benzaldehyde was added dropwise. After the addition was complete, it was stirred at room temperature for 1 hour. Stand for 30 minutes to separate the layers, separate the lower layer of oil, wash once with water, anhydrous MgSO 4 After drying and filtering, about 102 grams of brown oily benzaldoxime was obtained, with a yield of about 85%.

[0014] 2. Reduction and Salt Formation

[0015] In a 1-liter clean and dry four-neck flask, add 108 grams (0.9 moles) of benzaldehyde oxime, 600 milliliters of anhydrous methanol, and drop 2 drops of methyl orange indicator, cool the ice water to below 20 ° C, add dropwise HCl- methanol solution to keep the solution pink, while slowly adding 37.2 g (0.6 mol) NaBH 3 CN, heat will ...

Embodiment 2

[0017] 1. Oximation

[0018] In a 1-liter clean four-necked flask, add 600 ml of water, 72 g (1.02 moles) of hydroxylamine hydrochloride, stir and dissolve, add 156 g of 25% NaOH solution, and cool the ice water to about 20°C, between 20-30°C 108 g (1.02 mol) of benzaldehyde was added dropwise. After the addition was complete, it was stirred at room temperature for 1 hour. Stand for 30 minutes to separate the layers, separate the lower layer of oil, wash once with water, anhydrous MgSO 4 After drying and filtering, about 108 grams of brown oily benzaldoxime was obtained, with a yield of about 90%.

[0019] 2. Reduction and salt formation

[0020] In a 1-liter clean and dry four-neck flask, add 108 grams (0.9 moles) of benzaldehyde oxime, 600 milliliters of anhydrous methanol, and drop 2 drops of methyl orange indicator, cool the ice water to below 20 ° C, add dropwise HCl- methanol solution to keep the solution pink, while slowly adding 37.2 g (0.6 mol) NaBH 3 CN, heat wil...

Embodiment 3

[0022] 1. Preparation of benzaldoxime

[0023] In a 1-liter clean four-necked flask, add 600 milliliters of water, 72 grams (1.02 moles) of hydroxylamine hydrochloride, stir and dissolve, add 156 grams of 25% NaOH solution, and cool the ice water to about 20°C. 108 g (1.02 moles) of benzaldehyde was added dropwise. After the addition was completed, it was stirred at room temperature for 1 hour. Stand for 30 minutes to separate the layers, separate the lower layer of oil, wash once with water, anhydrous MgSO 4 Dry and filter to obtain about 108 grams of brown oily benzaldoxime, with a yield of about 90%, which is set aside.

[0024] 2. Preparation of N-benzyl hydroxylamine

[0025] In a 1-liter clean and dry four-neck flask, add 108 grams (0.9 moles) of benzaldehyde oxime, 600 milliliters of anhydrous methanol, and drop 2 drops of methyl orange indicator, cool the ice water to below 20 ° C, add HCl dropwise -Methanol solution to keep the solution pink while slowly adding 37....

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Abstract

The invention provides a method for preparing N-benzylhydroxylamine and hydrochloride thereof. The method is characterized in that oximation reaction is first carried out, which is to use water to dissolve hydroxylamine hydrochloride, add 25 percent NaOH solution, lower temperature to about 20 DEG C by use of ice water, drip benzaldehyde at a temperature between 20 and 30 DEG C and then stir for reaction at a room temperature; reactant is kept to stand for 30 minutes so as to be layered; oily matter in a lower layer is separated out and rinsed once, dried by use of anhydrous MgSO4 and filtered so as to obtain brown oily matter, namely benzaldehyde; the benzaldehyde is reduced by use of sodium cyanotrihydroborate, extracted and purified so as to obtain the N-benzylhydroxylamine; and finally the N-benzylhydroxylamine is salified by leading in hydrogen chloride so as to obtain the N-benzylhydroxylamine hydrochloride. The method has the advantages that raw materials for reaction are low in price and easy to get, and the method is mild in reaction, simple and stable in conditions and easy to expand production.

Description

technical field [0001] The invention relates to a preparation method of N-benzyl hydroxylamine and its hydrochloride. Background technique [0002] N-benzylhydroxylamine, also known as (N-)benzylamine. The melting point is 57-58°C. Its hydrochloride has a melting point of 110°C. N-benzyl hydroxylamine can be used as antioxidant and organic synthesis reagent, and its hydrochloride has become an important intermediate in organic chemistry. At home and abroad, it is commonly reduced by benzaldehyde oxime, or prepared by the reaction of hydroxylamine hydrochloride and benzyl chloride. The yield of the former is not high, and the latter has complicated procedures and high costs. Domestic technology in this area has not been improved very well, and there is no complete synthesis from the most easily available raw material benzaldehyde. Aiming at this blank, the present invention systematically expounds that benzaldehyde is used as a starting material, after oximation reaction...

Claims

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Application Information

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IPC IPC(8): C07C239/10
Inventor 谢宇胡金刚
Owner 江西豫章药业有限公司
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