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Process for the preparation of 4,5-dihydroxy-2-(4-methylbenzyl)isophthalonitrile

A technology of methyl benzyl and m-phthalocyanine, which is applied in the preparation of oxime, carboxylic acid nitrile, and carboxylate, and can solve the problems of limited commercial availability and difficult recovery of palladium catalysts, etc.

Pending Publication Date: 2021-07-23
ORION CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This creates residual palladium and the catalyst is difficult to recover
Limited commercial availability of bulk raw material 2-bromo-4-hydroxy-5-methoxybenzaldehyde

Method used

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  • Process for the preparation of 4,5-dihydroxy-2-(4-methylbenzyl)isophthalonitrile
  • Process for the preparation of 4,5-dihydroxy-2-(4-methylbenzyl)isophthalonitrile
  • Process for the preparation of 4,5-dihydroxy-2-(4-methylbenzyl)isophthalonitrile

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0110] Embodiment 1: Preparation of 2-methoxyphenyl 2-chloroacetate

[0111] 2-Methoxyphenol (20 mL), dichloromethane (60 mL) and water (28 mL) were added. 50% NaOH (8.0 mL) was slowly added at 0-10 °C. 2-Chloroacetyl chloride (10.0 mL) in dichloromethane (20 mL) was slowly added at 0-10 °C. 50% NaOH (7.8 mL) was added at 0-10 °C. 2-Chloroacetyl chloride (9.0 mL) in dichloromethane (10 mL) was slowly added at 0-10 °C. The mixture was stirred at 0-10°C for about 1 hour. 30% HCl (6 mL) and water (60 mL) were added at 0-10°C. The aqueous phase was separated. The organic phase was washed with water (60 mL), and 60 mL of dichloromethane was distilled off. Dichloromethane (100 mL) was added. 60 mL of dichloromethane was distilled off. The solution was used directly in the next step.

Embodiment 2

[0112] Embodiment 2: Preparation of 2-methoxyl-5-(4-methylbenzoyl)phenyl 2-chloroacetate

[0113] Dichloromethane (60 mL) and aluminum chloride (14.8 g) were added. 4-Methylbenzoyl chloride (16 mL) was slowly added at 0-10°C. Half of the solution obtained in Example 1 was slowly added at room temperature. The mixture was stirred overnight. Water (70 mL) and 30% HCl (16 mL) were slowly added at 0-10 °C. The aqueous phase was separated. The solution was used directly in the next step.

Embodiment 3

[0114] Embodiment 3: Preparation (3-hydroxyl-4-methoxyphenyl) (p-tolyl) ketone

[0115] From the solution obtained in Example 2, 50 mL of dichloromethane was distilled off. Methanol (132 mL) and 30% HCl (4.0 mL) were added. About 48 mL distilled off. The mixture was refluxed for 2 hours, then cooled to 0-5 °C. The compound was filtered, washed with methanol (30 mL), and dried under reduced pressure at 50-60 °C. The yield was 85.5% and the HPLC purity was 99.9%.

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PUM

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Abstract

The present disclosure relates to a process for the preparation of 4,5-dihydroxy-2-(4-methylbenzyl)isophthalonitrile, to use of a compound which is 2-methoxy-5-(4-methylbenzyl)phenol, (3-hydroxy-4-methoxyphenyl)(p-tolyl)methanone, 2-methoxy-5-(4-methylbenzoyl)phenyl 2-chloroacetate, 4-methylbenzoyl chloride, 2-methoxyphenyl 2-chloroacetate or 2-methoxyphenol in the preparation of 4,5-dihydroxy-2-(4-methylbenzyl)isophthalonitrile and to a compound which is 4-hydroxy-5-methoxy-2-(4-methylbenzyl)isophthalaldehyde dioxime or 4-hydroxy-5-methoxy-2-(4-methylbenzyl)isophthalaldehyde and use thereof in the preparation of 4,5-dihydroxy-2-(4-methylbenzyl)isophthalonitrile. 4,5-Dihydroxy-2-(4-methylbenzyl)isophthalonitrile is a COMTinhibitor.

Description

technical field [0001] The present disclosure relates to a process for the preparation of 4,5-dihydroxy-2-(4-methylbenzyl)isophthalocyanine, involving the compound 2-methoxy-5-(4-methylbenzyl)phenol, (3 -Hydroxy-4-methoxyphenyl)(p-tolyl)methanone, 2-methoxy-5-(4-methylbenzoyl)phenyl 2-chloroacetate, 4-methylbenzoyl chloride , the use of 2-methoxyphenyl 2-chloroacetate or 2-methoxyphenol in the preparation of 4,5-dihydroxy-2-(4-methylbenzyl) isophthalocyanine, and relates to compound 4 -Hydroxy-5-methoxy-2-(4-methylbenzyl)isophthalaldehyde dioxime or 4-hydroxy-5-methoxy-2-(4-methylbenzyl)isophthalaldehyde and its use in the preparation of 4,5-dihydroxy-2-(4-methylbenzyl)isophthalocyanine. 4,5-Dihydroxy-2-(4-methylbenzyl)isophthalocyanine is a catechol O-methyltransferase (COMT) inhibitor. [0002] Background of the invention [0003] The compound 4,5-dihydroxy-2-(4-methylbenzyl)isophthalocyanine of formula (1A) has been disclosed in WO2013 / 175053. [0004] [0005] 4,5-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/53C07C251/36C07C255/55
CPCC07C253/00C07C249/08C07C251/48C07C67/14C07C67/293C07C45/65C07C41/18C07C255/53C07C255/55C07C69/63C07C49/255C07C43/23
Inventor E·昆普莱宁I·莱蒂宁J·皮斯蒂宁
Owner ORION CORPORATION
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