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A kind of preparation method of Procaterol hydrochloride
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A technology of procaterol hydrochloride and methamphetamine butyryl, which is applied in the field of drug synthesis, can solve the problems of high production cost, achieve the effects of low price, reduce production cost, and improve preparation efficiency
Active Publication Date: 2021-09-24
佛山市隆信医药科技有限公司
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[0004] The invention provides a preparation method of Procaterol hydrochloride, which solves the problem of high production cost of the existing Procaterol hydrochloride
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Embodiment 1
[0049] The preparation of the present embodiment 5-(2-bromobutyryl)-8-hydroxyquinolone
[0050] Add carbon disulfide (600mL), 8-hydroxyquinoline nitrogenoxide (79.59g, 0.5mol), 2-bromobutyryl bromide (344.85g, 1.50mol) and aluminum trichloride ( 133.34g, 1.00mol), reacted for 3 hours at 25°C, filtered, recrystallized and dried with 800ml 95% ethanol to obtain yellow crystal 5-(2-bromobutyryl)-8-hydroxyquinolone (100.8g), yield 78%, Its purity was greater than 98% by HPLC.
[0053] This embodiment is the preparation of 5-(2-bromobutyryl)-8-hydroxyquinolone
[0054] Add nitrobenzene (550mL), 8-hydroxyquinoline nitrogen oxide (79.59g, 0.5mol), 2-bromobutyryl chloride (278.18g, 1.50mol) and aluminum trichloride to a 1000mL there-necked flask with mechanical stirring (133.34g, 1.00mol), reacted at 70°C for 6 hours, filtered, recrystallized from 700ml 95% ethanol and dried to obtain yellow crystal 5-(2-bromobutyryl)-8-hydroxyquinolone (96.15g), yield 75% , and its purity was greater than 98% as detected by HPLC.
Embodiment 3
[0056] Preparation of 5-(2-methylisopropylaminobutyryl)-8-hydroxyquinolone
[0057] Add methanol (600mL), 5-(2-bromobutyryl)-8-hydroxyquinolone (92.97g, 0.3mol) prepared in Example 1, isopropylamine (26.60g, 0.45 mol), be warming up to 60 DEG C and react for 8 hours, be down to room temperature, the pH of the reaction solution is adjusted to 2 with hydrochloric acid, and the solid is precipitated, filtered and washed with water to obtain 5-(2-methylisopropylaminobutyryl)-8-hydroxyquinolone ( 77.85g), its purity was greater than 99% as detected by HPLC, and its yield was 90%.
[0058] The detection result of 5-(2-methylisopropylamine butyryl)-8-hydroxyquinolone proton NMR spectrum is: 1 HNMRδ: 8.24~8.21(d, J=12Hz, 1H, ArH), 7.18~7.16(d, J=8Hz, 1H, ArH), 6.95~6.93(d, J=8Hz, 1H, ArH), 6.79~6.77 (d,J=8Hz,1H,ArH),11.43(s,1H,NH),4.13~4.11(m,1H,CH),3.98~3.66(q,J=4Hz,1H,CH),1.58~1.75 (m,2H,CH 2 ), 1.51~1.54 (t, J=8Hz, 6H, CH 3 ),0.71~0.74(t,J=8Hz,3H,CH 3 )
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Abstract
The invention discloses a preparation method of Procaterol hydrochloride, which comprises obtaining 5-(2-bromobutyryl)-8-hydroxyquinolone by reacting 8-hydroxyquinoline nitrogenoxide with 2-bromobutyryl halide, and then amine Decomposition to obtain 5-(2-methylisopropylamine butyryl)-8-hydroxyquinolone, then hydrogenation reduction to obtain Procaterol, and finally salify with hydrochloric acid to obtain Procaterol hydrochloride. In the preparation method of Procaterol hydrochloride provided by the invention, the 8-hydroxyquinoline nitrogenoxide that is cheap and easy to obtain is used as starting material to prepare Procaterol hydrochloride, which reduces the production cost of Procaterol hydrochloride, and The preparation steps of 8-acetoxyquinolone and 8-hydroxyquinolone in the conventional route are omitted, the preparation steps of Procaterol hydrochloride are simplified, and the reduction stereoselectivity is improved, thereby saving preparation time, improving preparation efficiency, and being suitable for large-scale industrial production.
Description
technical field [0001] The invention belongs to the technical field of drug synthesis, and in particular relates to a preparation method of Procaterol Hydrochloride. Background technique [0002] Procaterol hydrochloride was invented and manufactured by Otsuka Pharmaceutical Co., Ltd., Japan, and is a bronchodilator. It is suitable for bronchial asthma, asthmatic bronchitis, acute bronchitis with increased bronchial reactivity, and chronic obstructive pulmonary disease. [0003] There are few published patent documents about the preparation of this product. The original Japanese Otsuka patent US4026897 describes the use of 2,8-dihydroxyquinoline as a starting material to prepare Procaterol hydrochloride through rearrangement, condensation, hydrogenation reduction, and salification. This preparation route adopts 2,8-dihydroxyquinoline with high cost as the starting material, and the hydrogenation selectivity is not high, resulting in high production cost of procaterol hydroc...
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