Process for preparing 3-amino-2-naphthoic acid compound

A preparation process, a technology of naphthoic acid, applied in the preparation of carbamic acid derivatives, the preparation of organic compounds, the preparation of cyanide reactions, etc., can solve the problems of high preparation cost, poor applicability, unstable reaction, etc., and reduce the use of special equipment. The effect of using, wide application and reducing production cost

Active Publication Date: 2019-05-24
SHANGHAI JINGCHUN BIOCHEM TECH CO LTD
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Problems solved by technology

[0004] The technical problem to be solved by the present invention is: the synthesis method of existing 3-amino-2-naphthoic acid compounds has problems such as unstable reaction, poor applicability, and high preparation cost

Method used

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  • Process for preparing 3-amino-2-naphthoic acid compound

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Embodiment

[0030] A kind of preparation technology of 3-amino-2-naphthoic acid compounds:

[0031] (1) 15.84g of dimethyl maleate was dissolved in 300mL of dichloromethane, and the resulting solution was cooled with an ice bath, and 24.24g of tri-n-butylphosphine was added dropwise to the low-temperature solution. Rise to room temperature, and continue to stir the reaction for more than 0.5h. Dissolve 13.4g of o-phthalaldehyde in 200mL of dichloromethane solution, and slowly add the mixture obtained above under cooling in an ice bath, then add 1.52g of DBU dropwise, and stir the resulting mixture at room temperature for 3h. Quench the reaction with 400mL ice water, separate the organic phase, extract the aqueous phase twice with 200mL dichloromethane, combine the organic phases, wash with 150mL saturated brine, dry the organic phase with anhydrous sodium sulfate for 2h, concentrate under reduced pressure, and the product column After separation by chromatography, 22.3 g of dimethyl 2,3-...

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Abstract

The invention discloses a process for preparing a 3-amino-2-naphthoic acid compound, which is characterized in that a condensed ring-2, 3-dimethyl naphthalene dicarboxylate is prepared from phthalic dicarboxaldehyde under the action of tri-n-butyl phosphine; then, the condensed ring-2, 3-dimethyl naphthalene dicarboxylate is hydrolyzed to 2, 3-monomethyl naphthalene dicarboxylate under an alkalinecondition; then, the carboxyl group is converted to the amino group through DPPA reaction to obtain 3-tert-formamido-2-naphthoate methyl; finally, the ester is hydrolyzed, and the tert-butoxycarbonylgroup is further removed to obtain the 3-amino-2-naphthoic acid. The method has mild reaction conditions, is suitable for different substrates, does not need to use high-temperature and high-pressurekettle equipment, reduces the safety risk in the production process, reduces the equipment investment, reduces the production energy consumption, and is suitable for large-scale production.

Description

technical field [0001] The invention relates to a synthesis method of fused-ring aromatic carbamic acid compounds, in particular to a preparation process of 3-amino-2-naphthoic acid compounds, belonging to the technical field of organic synthesis. Background technique [0002] 3-Amino-2-naphthoic acid compound is an important class of fused-ring aromatic hydrocarbon organic compounds. Its molecular structure is unique. It contains not only amino active groups but also carboxyl active functional groups in the molecule. Two chemical functional groups with different characteristics are distributed in the on the naphthalene ring. 3-Amino-2-naphthoic acid compound is not only a useful synthetic intermediate, but also has very high application value in the fields of biology, medicine, dyes, pesticides and fine chemicals because of its unique chemical structure. [0003] Heterocycles, 2012, 86 (1), 425-433 and Journal of Organic Chemistry, 1994, 59 (4), 823-828 and Bulletin of the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/68C07C227/20C07C67/343C07C69/76C07C67/313C07C271/30C07C269/04C07C269/06
Inventor 海龙徐久振姜苏凌青
Owner SHANGHAI JINGCHUN BIOCHEM TECH CO LTD
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