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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: 2003-09-24
DAICEL CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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

Examples

Experimental program
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Effect test

Embodiment 1

[0118] Cyclopentane (1ml), tert-butyronitrile (1mmol), N-hydroxyphthalimide (0.2mmol) and acetic acid (1ml) were put into a flask and heated under an argon atmosphere (1atm=0.101 MPa) 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

[0120] Cyclohexane (1ml), tert-butyronitrile (1mmol), N-hydroxyphthalimide (0.2mmol) and acetic acid (1ml) were put into the flask and heated under an argon atmosphere (1atm=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 16%, 10%, 3% and 2%, respectively.

Embodiment 3

[0122] Cyclohexane (1ml), tert-butyronitrile (1mmol), 4-chloro-N-hydroxyphthalimide (0.2mmol) and acetic acid (1ml) were put into a flask and heated at 80°C under an argon atmosphere (1 atm = 0.101 MPa) 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 13%, 9%, 2% and 2%, respectively.

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Abstract

A method for producing an organic compound by making at least one of (A) a compound capable of generating free radicals and (B) an ester and a salt of nitrous acid have, in its ring structure, compositionally represented by the above formula (i) The nitrogen-containing cyclic compound of the skeleton is reacted in the presence of the ring compound, wherein X is one of an oxygen atom and an -OR group, and wherein R is one of a hydrogen atom and a hydroxyl protection group. Examples of nitrogen-containing cyclic compounds include cyclic imide compounds having a cyclic imide skeleton represented by the above formula (I), wherein n is one of 0 and 1; X is one of an oxygen atom and an -OR group species, and wherein R is one of a hydrogen atom and 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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IPC IPC(8): C07B47/00C07B61/00C07C5/42C07C15/44C07C29/48C07C33/20C07C45/28C07C47/54C07C47/542C07C49/395C07C49/403C07C49/413C07C49/78C07C67/035C07C69/14C07C69/157C07C201/00C07C201/08C07C205/04C07C205/16C07C207/02C07C249/06C07C251/40C07C251/44C07C251/48C07C253/02C07C255/50
CPCC07B47/00C07C201/00C07C249/06C07C2601/08C07C2601/14C07C2601/18C07C2601/20Y02P20/55C07C251/44C07C251/48C07C207/02
Inventor 石井康敬中野达也岩浜隆裕
Owner DAICEL CHEM IND LTD
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