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Method for preparing nitro orotic acid

A technology of nitroorotic acid and nitro, which is applied in the field of preparation of nitroorotic acid and compounds, can solve problems such as reaction system explosion, and achieve the effect of reducing risk and safety advantages

Active Publication Date: 2014-12-17
HAIZHENG CHEM NANTONG CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In this industrial method, nitric acid and 6-methyluracil are first nitrated into 5-nitro-6-methyluracil, and then the temperature is slowly raised to 110°C for oxidation reaction of 5-nitro-6-methyluracil. A large amount of heat is released during the process. If the temperature cannot be well controlled, the reaction system may explode violently.

Method used

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  • Method for preparing nitro orotic acid
  • Method for preparing nitro orotic acid

Examples

Experimental program
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Effect test

Embodiment 1

[0029] The preparation of embodiment 1 nitroorotic acid

[0030] Mix and stir 1.8kg (18.18mol) of concentrated sulfuric acid (98%) and 17kg (142.9mol) of chloroform, then add 1.5kg (11.6mol) of 6-methyluracil at one time and heat up to 50°C. Control the temperature at 50-55°C, add 9 kg (140 mol) of concentrated nitric acid (98%) dropwise to the mixture, and after the dropwise addition, reflux and stir at this temperature for 30 hours (the reaction is complete as detected by HPLC).

[0031] Stop heating after the reaction is complete, add 3kg of water into the system, keep the system temperature not exceeding 35°C, separate layers, and the chloroform layer can be directly recycled and reused.

[0032] The water layer was cooled to 1-5°C, kept at this temperature for 3 hours, then suction filtered and dried to obtain the product.

[0033] Yield: 1.96kg (84.1%);

[0034] Purity: 97.6% (HPLC).

Embodiment 2

[0035] The preparation of embodiment 2 nitroorotic acid

[0036] Mix and stir 1.8kg (18.18mol) of concentrated sulfuric acid (98%) and 17kg (142.9mol) of chloroform, then add 1.5kg (11.6mol) of 6-methyluracil at one time and heat up to 50°C. Control the temperature at 50-55°C, add 4.5kg (70mol) of concentrated nitric acid (98%) dropwise to the mixture, and after the dropwise addition, reflux and stir at this temperature for 30 hours (the reaction is complete as detected by HPLC).

[0037] Stop heating after the reaction is complete, add 3kg of water into the system, keep the system temperature not exceeding 35°C, separate layers, and the chloroform layer can be directly recycled and reused.

[0038] The water layer was cooled to 1-5°C, kept at this temperature for 3 hours, then suction filtered and dried to obtain the product.

[0039] Yield: 1.31kg (56%);

[0040] Purity: 97.0% (HPLC).

Embodiment 3

[0041] The preparation of embodiment 3 nitroorotic acid

[0042] Mix and stir 1.8kg (18.18mol) of concentrated sulfuric acid (98%) and 17kg (142.9mol) of chloroform, then add 1.5kg (11.6mol) of 6-methyluracil at one time and heat up to 50°C. Control the temperature at 50-55°C, add 10.5kg (163mol) of concentrated nitric acid (98%) dropwise to the mixture, and after the dropwise addition, reflux and stir at this temperature for 30 hours (HPLC detects that the reaction is complete).

[0043] Stop heating after the reaction is complete, add 3kg of water into the system, keep the system temperature not exceeding 35°C, separate layers, and the chloroform layer can be directly recycled and reused.

[0044] The water layer was cooled to 1-5°C, kept at this temperature for 3 hours, then suction filtered and dried to obtain the product.

[0045] Yield: 1.86kg (80.1%);

[0046] Purity: 97.7% (HPLC).

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Abstract

The invention discloses a method for preparing nitro orotic acid, and belongs to the field of chemical synthesis. According to the method, the conventional method for preparing the nitro orotic acid is improved. The method is characterized in that the nitro orotic acid (III) is obtained by performing nitratlon reaction of 6-methyl urea pyrimidine (I) and subsequent oxidation reaction of 5-nitryl-6-methyl urea pyrimidine (II) at the temperature of between 50 and 80 DEG C in the presence of a specific organic solvent and a catalyst, wherein the organic solvent is selected from at least one of chloroform, dichloroethane, dichloromethane, n-pentane, normal hexane or normal heptane; and the catalyst is acid, and preferably is concentrated sulfuric acid. By the method, the reaction can be performed stably at the temperature of between 50 and 80 DEG C, so that risk of a production process is reduced greatly, and the method has the great advantage in the aspect of safety. In addition, the product is high in purity, so that the purification coat is reduced, and the yield of the process is improved.

Description

technical field [0001] The invention relates to a method for preparing a compound, in particular to a method for preparing nitroorotic acid. It belongs to the field of chemical synthesis. Background technique [0002] Nitroorotic acid is a key intermediate for the synthesis of dipyridamole, which is a precursor for the synthesis of Persantin and Aggrenox. [0003] Several methods for the preparation of nitroorotic acid are known in the prior art: [0004] Nitroorotic acid can be prepared by the nitration reaction of orotic acid, and early reports (M.Bachstez, Ber.dtsch.chem.Ges.63, 1930, 1000 and H.Biltz, Ann 456, 1924, 165) showed that this The yield of the first reaction is low. Although Rolf et al. (CN 101812023) of Boehringer Ingelheim optimized this reaction and increased the reaction yield to 90%, but due to the high cost of raw materials, this method is not currently available. Not used on a large scale in industry. [0005] F.G.Fshcher et al. (Ann.572,1951,217) r...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/557
Inventor 包如胜蒋富国戴炜锷赵宸良李劲徐坚勇
Owner HAIZHENG CHEM NANTONG CO LTD
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