Method for the preparation of organic nitrates

A technology of nitric acid and esterification of hydroxyl groups, which is applied in the field of preparation of organic nitrates, and can solve the problems of not providing yields, etc.

Inactive Publication Date: 2011-06-01
LONZA LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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  • Method for the preparation of organic nitrates
  • Method for the preparation of organic nitrates
  • Method for the preparation of organic nitrates

Examples

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Embodiment 1

[0084] Example 1: Preparation of 1,4-butanediol monoacetate with liquid catalyst

[0085] Add 1,4-butanediol (400g, 4.4mol), acetic acid (254.0g, 4.2mol) and CH to a 10L glass container equipped with a stirring blade at 20°C 2 Cl 2 (4.0kg). To this clear solution, 98% sulfuric acid (21.2 g, 0.22 mol) was added dropwise within 5 minutes, and then the resulting cloudy mixture was stirred at 20°C for 6 hours. Use 5% Na 2 CO 3 The reaction mixture was extracted with an aqueous solution (2x1300 mL) to remove unreacted acetic acid. The organic phase was then washed with water (2x500 mL). After removing the solvent under vacuum (35°C, 600 mbar), a liquid product (289.3 g) was obtained. GC analysis (FID): 1,4-butanediol monoacetate 91.8%-area.

Embodiment 2

[0086] Example 2: Preparation of 1,4-butanediol monoacetate with solid catalyst

[0087] Add 1,4-butanediol (240.1g, 2.7mol), acetic acid (152.0g, 2.5mol), CH to a 10L glass container equipped with a stirring blade and a reflux condenser at 20°C 2 Cl 2 (1.2kg) and amberlyst 36 (12.0g). The resulting clear mixture was heated to reflux. After 24 hours, cool the mixture, filter off the solid catalyst, and use 5% Na 2 CO 3 The organic phase was washed with aqueous solution (2*400 mL) and water (2*170 mL). The solvent was removed in vacuo to obtain 179.4 g of clear liquid. According to GC analysis (FID), 1,4-butanediol monoacetate was obtained with a yield of 92.0%.

Embodiment 3

[0088] Example 3: Preparation of 4-hydroxybutyl 4-nitrobenzoate

[0089] Under nitrogen atmosphere, add 1,4-butane-diol (90.0g, 1.0mol, 3.7eq.), 4-(dimethylamino)-pyridine (DMAP, 0.3g), acetone (300mL) and triethylamine in sequence (23.4g) and cooled to -5°C. The p-nitrobenzoyl chloride (37.1 g, 0.27 mol, 1 eq.) in acetone (200 mL) was added dropwise while maintaining the internal temperature 2 Cl 2 (500 mL) was added to the residue and the resulting mixture was washed with brine (3x300 mL). Take Na 2 SO 4 The organic residue was dried, filtered and the solvent was removed under reduced pressure to dryness. The resulting product 4-hydroxybutyl 4-nitrobenzoate was a yellow solid (31.5 g, 66%).

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Abstract

The present invention relates to a process for the preparation of organic nitrates having at least one nitryloxy and at least one hydroxy group, wherein the at least one hydroxy group may be present in form of an esterified hydroxy residue, the latter being esterified with an acid other than nitric acid.

Description

Technical field [0001] The invention relates to a process for preparing organic nitrate esters with at least one nitroxyl oxide and at least one free hydroxyl group or esterified hydroxyl residue. The term "esterified hydroxyl residue" here and below means a hydroxyl group esterified with a non-nitric acid acid or anhydride. The hydroxyl groups esterified with nitric acid are called nitroxyl groups. Background technique [0002] Organic nitrate esters with at least one nitroxyl group (ester of alcohol and nitric acid) and at least one free hydroxyl group are valuable building blocks. Many pharmacologically active compounds contain nitroxyl groups, which stimulate endogenous nitric oxide production and / or become substrates for nitric oxide synthase and / or cytochrome P450 by releasing nitric oxide (nitric oxide donor). Things. Anti-inflammatory agents such as 2-(S)-(6-methoxy-2-naphthyl)-propionic acid (naproxen) in combination with the above-mentioned building blocks are provid...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C201/02C07C201/12C07C203/04C07C205/57
CPCC07C205/57C07C203/04C07C201/02C07C201/12
Inventor 沃尔特·布瑞登多米尼克·米歇尔威廉·奎特曼法比奥·拉伊诺内潘杰辉方航兵宋英霞
Owner LONZA LTD
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