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A technology of methylquinoline and intermediates, which is applied in the field of preparation of baquiprime, and achieves the effects of long reaction time, high yield and easy availability of raw materials
Active Publication Date: 2015-09-09
QINGDAO VLAND BIOTECH INC
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At present, there is no manufacturer's application for baquiprime in China, and it has a broad market prospect
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[0028] The synthetic method step of baquiprime among the present invention is as follows:
[0029] Using m-toluidine as the starting material, 8-amino-7-methylquinoline (intermediate III) was obtained through Skraup reaction, nitration and nitro reduction, and 5-dimethoxyquinoline (intermediate III) was obtained through Mannich reaction using uracil as the starting material. Methylaminomethyluracil hydrochloride (intermediate IV), and then react with 8-amino-7-methylquinoline (intermediate III) through condensation, Eschweiler-Clarke methylation, chlorination, and ammonolysis in eight steps Synthesis of baquiprine. Its specific reaction route is as follows figure 1 shown.
Embodiment 1
[0032] (1) Add glycerin (230mL, 3.1mol), m-toluidine (80.3mL, 0.75mol), iodine (9.5g, 37.5mmol) into a 1L three-necked flask, stir mechanically, and slowly add concentrated sulfuric acid (165mL, 3.1 mol), warm up to 140°C and reflux for 2 hours after dropping, add ice water 200mL to dilute after cooling, add 30% sodium hydroxide solution dropwise under ice bath, neutralize to pH>9, add ethyl acetate 500mL for extraction, water 300mL ×3 washed, added anhydrous sodium sulfate to dry, suction filtered, and evaporated to dryness of ethyl acetate to obtain brown oily liquid 1 (97g, yield 90.3%), that is, 7-methylquinoline (intermediate Ⅰ).
[0033] (2) Add concentrated sulfuric acid (230mL, 4.3mol) into a 1L three-necked flask, add intermediate I (97g, 0.68mol) under ice bath and mechanical stirring, and slowly add 65% concentrated nitric acid (54mL, 0.82mol) dropwise after dissolution ), stirred at room temperature for 1 h after dropping, poured the reaction solution into 2 L of i...
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Abstract
The invention provides a preparation method of baquiloprim. The preparation method is mild in conditions, convenient to operate, high in yield and low in cost. Specifically the preparation method comprises the following steps: taking m-toluidine as an initial raw material, performing a Skraup reaction, nitration, and nitroreduction to obtain an intermediate 8-amino-7-methylquinoline; taking uracil as the initial raw material, and performing a Mannich reaction to obtain an intermediate 5-dimethylamine methyl uracil hydrochloride; performing condensation, Eschweiler-Clarke methylation, chlorination and aminolysis and the like on the intermediate 8-amino-7-methylquinoline and the intermediate 5-dimethylamine methyl uracil hydrochloride to synthesize baquiloprim. The preparation method is easily available in raw materials, easy to operate and favorable for industrialization production.
Description
technical field [0001] The invention belongs to the field of veterinary antibacterial synergists and relates to a preparation method of baquiprime. Background technique [0002] Sulfa drugs are the most widely used drugs in the global veterinary drug industry. In order to improve antibacterial activity and reduce drug resistance, they must be used in combination with antibacterial synergists. Therefore, antibacterial synergists are widely used and have a huge demand. [0003] Trimethoprim is a commonly used antibacterial synergist. Its disadvantages are short half-life and fast metabolic elimination. It can be combined with sulfa drugs with long half-lives such as sulfamethoxine, sulfadimethoxine, and sulfa-metamethoxine. When used, it can only play a short-term synergistic effect, which affects the clinical efficacy. [0004] The Wellcome Foundation company transformed the 5-substituted phenyl group of trimethoprim into a substituted quinolinyl group to obtain 5-[8-(dimeth...
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