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Process for producing organic compound using nitrite

A technology for organic compounds and nitroso compounds, which is applied in the preparation of organic compounds, organic chemical methods, and preparation of nitro compounds, and can solve problems such as low space-time yields and harsh reaction conditions

Inactive Publication Date: 2009-05-20
DAICEL CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method requires harsh reaction conditions and shows low space-time yields

Method used

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  • Process for producing organic compound using nitrite
  • Process for producing organic compound using nitrite
  • Process for producing organic compound using nitrite

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0128] Cyclopentane (1ml), tert-butyl nitrite (1mmol), N-hydroxyphthalimide (0.2mmol) and acetic acid (1ml) were put into a flask and heated at 80°C under an argon atmosphere (1atm =0.101MPa) and stirred for 20 hours. Analysis of the resulting reaction mixture revealed formation of cyclopentanone oxime, nitrocyclopentane, cyclopentanone and cyclopentyl acetate in yields of 4%, 2%, 3% and less than 1%, respectively.

Embodiment 2

[0130] Cyclohexane (1ml), tert-butyl nitrite (1mmol), N-hydroxyphthalimide (0.2mmol) and acetic acid (1ml) were put into a flask and heated at 80°C under an argon atmosphere (1atm =0.101MPa) and stirred for 20 hours. Analysis of the resulting reaction mixture revealed the formation of cyclohexanone oxime, nitrocyclohexane, cyclohexanone and cyclohexyl acetate in yields of 16%, 10%, 3% and 2%, respectively.

Embodiment 3

[0132] Cyclohexane (1ml), tert-butyl nitrite (1mmol), 4-chloro-N-hydroxyphthalimide (0.2mmol) and acetic acid (1ml) were put into a flask and heated at 80°C under argon Stir in an air atmosphere (1 atm = 0.101 MPa) for 20 hours. Analysis of the resulting reaction mixture revealed the formation of cyclohexanone oxime, nitrocyclohexane, cyclohexanone and cyclohexyl acetate in yields of 13%, 9%, 2% and 2%, respectively.

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Abstract

A process produces an organic compound by allowing (A) a compound capable of generating a free radical to react with (B) at least one of esters and salts of nitrous acid in the presence of a nitrogen-containing cyclic compound constitutively having a skeleton represented by following Formula (i) in its ring: <CHEM> wherein X is an oxygen atom or an -OR group, and wherein R is a hydrogen atom or a hydroxyl-protecting group. Examples of the nitrogen-containing cyclic compound are cyclic imide compounds having a cyclic imide skeleton represented by following Formula (I): <CHEM> wherein n is 0 or 1; X is an oxygen atom or an -OR group, and wherein R is a hydrogen atom or a hydroxyl-protecting group.A process produces an organic compound by allowing (A) a compound capable of generating a free radical to react with (B) at least one of esters and salts of nitrous acid in the presence of a nitrogen-containing cyclic compound constitutively having a skeleton represented by following Formula (i) in its ring: <CHEM> wherein X is an oxygen atom or an -OR group, and wherein R is a hydrogen atom or a hydroxyl-protecting group. Examples of the nitrogen-containing cyclic compound are cyclic imide compounds having a cyclic imide skeleton represented by following Formula (I): <CHEM> wherein n is 0 or 1; X is an oxygen atom or an -OR group, and wherein R is a hydrogen atom or a hydroxyl-protecting group.

Description

technical field [0001] The present invention relates to a method for producing organic compounds each having, for example, a nitrogen-containing group, an oxygen-containing group, or a carbon-carbon unsaturated bond-containing group, using nitrite and / or nitrite salts. Background technique [0002] Oximes and other organic compounds each having a nitrogen-containing group can be used as an intermediate substance of a monomer for producing a polymer compound or as an intermediate in synthesizing fine chemicals. For example, cycloalkanone oxime is a very important polyamide intermediate material. These cycloalkanone oximes have generally been produced by methods such as the dehydration condensation of cycloalkanones and hydroxylamines, the catalytic hydrogenation of nitrocycloalkanones in the presence of palladium catalysts, or the conversion of hydroxylaminocycloalkanes A method of air oxidation in the presence of cobalt. However, these methods require rather expensive star...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B47/00C07C41/00C07C43/00C07C249/04C07B61/00C07C5/42C07C15/44C07C29/48C07C33/20C07C45/28C07C47/54C07C47/542C07C49/395C07C49/403C07C49/413C07C49/78C07C67/035C07C69/14C07C69/157C07C201/00C07C201/08C07C205/04C07C205/16C07C207/02C07C249/06C07C251/40C07C251/44C07C251/48C07C253/02C07C255/50
CPCC07C2101/18C07C2101/08C07C201/00C07B47/00C07C2101/14C07C207/02C07C249/06C07C2101/20C07C2601/08C07C2601/14C07C2601/18C07C2601/20Y02P20/55C07C251/44C07C251/48
Inventor 石井康敬中野达也岩浜隆裕
Owner DAICEL CHEM IND LTD
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