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Production of n-substituted aromatic hydroxylamines

A kind of aromatic hydroxylamine, aromatic nitrogen technology, applied in the production field of N-substituted aromatic hydroxylamine, can solve the problem of insufficiency of economy, yield is not optimal etc.

Active Publication Date: 2022-07-15
SOLVIAS AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method is not yet economical as two sequential chemical steps are required and the yields are not yet optimal

Method used

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  • Production of n-substituted aromatic hydroxylamines
  • Production of n-substituted aromatic hydroxylamines
  • Production of n-substituted aromatic hydroxylamines

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Example 1 : Production of methyl hydroxy (phenyl) carbamate

[0056] 50 mg of 5% Pt-carbon catalyst was placed in a glass vessel with 15 mg of 50% aqueous hypophosphorous acid and 1 ml of deionized water and stirred for 10 minutes.

[0057] exist In a glass flask, 1.04 g of nitrobenzene was placed in 30 ml of cyclopentyl methyl ether, and 1.68 g (1.4 equiv.) of disodium hydrogen phosphate and 1.04 g (1.3 equiv.) of methyl chloroformate were added. then in The catalyst suspension was rinsed with 4 ml of deionized water in a glass flask and hydrated for 3 hours at a temperature of 22° C. and a hydrogen pressure of 4 bar. After inertizing the apparatus with nitrogen, 1 ml of methanol was added and stirred for 15 minutes to destroy excess methyl chloroformate. The solid was then filtered off and washed with 20 ml of cyclopentyl methyl ether. The filtrate was dried over sodium sulfate and evaporated in vacuo at 60°C. This yielded 1.43 g (101% theoretically possible) ...

Embodiment 2

[0058] Example 2 : Production of methyl(2-(((1-(4-chlorophenyl)-1H-pyrazol-3-yl)oxy)methyl)phenyl)(hydroxy)carbamate

[0059] 83 mg of 5% Pt-carbon catalyst was placed in a glass vessel with 164 mg of 50% aqueous hypophosphorous acid and 1 ml of deionized water and stirred for 10 minutes.

[0060] Place 1.65 g of 1-(4-chlorophenyl)-3-((2-nitrobenzyl)oxy)-1H-pyrazole on To 30 ml of cyclopentyl methyl ether in a glass flask, 0.994 g (1.4 equiv.) of disodium hydrogen phosphate and 0.614 g (1.3 equiv.) of methyl chloroformate were added. then in The catalyst suspension was rinsed with 4 ml of deionized water in a glass flask and hydrated for 7 hours at a temperature of 22° C. and a hydrogen pressure of 4 bar. After inertizing the apparatus with nitrogen, 1 ml of methanol was added and stirred for 15 minutes to destroy excess methyl chloroformate. The solid was then filtered off and washed with 20 ml of cyclopentyl methyl ether. The filtrate was dried over sodium sulfate and...

Embodiment 3

[0061] Example 3 : Production of methyl(2-(((1-(4-chlorophenyl)-1H-pyrazol-3-yl)oxy)methyl)phenyl)(hydroxy)carbamate

[0062] 1086 mg of 5% Pt-carbon catalyst (water content: 54%) was placed in a glass vessel with 3 ml of deionized water and 550 mg of 50% aqueous hypophosphorous acid and stirred for 10 minutes.

[0063] In a 100ml stirring autoclave, place 10.00g 1-(4-chlorophenyl)-3-((2-nitrobenzyl)oxy)-1H-pyrazole in 50ml 2-methyltetrahydrofuran, 6.03 g (1.4 equiv.) disodium hydrogen phosphate and 3.73 g (1.3 equiv.) methyl chloroformate were added. The catalyst suspension was then rinsed with 2 ml of deionized water in the autoclave and hydrated at a temperature of 21° C. and a hydrogen pressure of 7 bar. After 1.5 hours, hydrogen uptake ceased. After inertizing the apparatus with nitrogen, 1 ml of methanol was added and stirred for 20 minutes to destroy excess methyl chloroformate. The reaction mixture was then rinsed with 20 ml of 2-MeTHF and 5 ml of water from the a...

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Abstract

An economical one-step method for producing N-substituted aromatic hydroxylamines of formula (I) with hydrogen: R-N(OH)-C(=O)-(O)R 1 (I), the method in which N of formula (I) is produced by catalytic hydration with a possibly modified hydration catalyst in an aprotic solvent and in the presence of a haloformate, in some cases a base ‑Substituted aromatic hydroxylamines.

Description

technical field [0001] The present invention relates to a process for the preparation of N-alkoxycarbonyl-substituted aromatic hydroxylamines or N-aryloxycarbonyl-substituted aromatic hydroxylamines by catalytic hydration in an inert solvent, in a haloformate and possibly It is carried out with hydrogen gas and modified hydration catalyst (optional) in the presence of base. Background technique [0002] N-substituted aromatic hydroxylamines are important chemicals for the production of pesticides, for example. The production is carried out by a two-stage reaction, ie, the aromatic hydroxylamine is first formed, and in the second step, the substitution is carried out on the nitrogen of the aromatic hydroxylamine. The production of aromatic hydroxylamines is generally carried out by catalytic hydration of nitroaromatics, catalytic transfer hydration (eg with a rhodium catalyst and hydrazine as hydrogen donor) or by zinc reduction of nitroaromatics. Typically, secondary produ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C269/00C07C271/28C07D231/22
CPCC07C269/00C07D231/22C07C271/28C07D257/06
Inventor H·斯坦纳
Owner SOLVIAS AG