Preparation method of indacaterol intermediate diethylbenzene
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A technology for o-diethylbenzene and o-ethylacetophenone, which is applied in the field of preparing o-diethylbenzene and can solve problems such as large environmental pollution
Inactive Publication Date: 2014-07-02
TIANJIN INSTITUTE OF PHARMA RESEARCH
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[0008] Journal of the American Chemical Society, 1949, vol.71, p.1362-1366, using o-ethyl acet
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Embodiment 1
[0022] o-Ethylacetophenone (29.6g, 0.20mol), 80% hydrazine hydrate (97.7ml, 1.6mol) and absolute ethanol (400ml) were mixed, magnetically stirred, and refluxed at 25°C for 2-6 hours. After the reaction, add appropriate amount of distilled water, extract with ethyl acetate, wash with saturated brine, anhydrous Na 2 SO 4 Drying and rotary evaporation gave white crystal II (28.9 g, yield 89.1%). 1H-NMR (CDCl3) δ7.24(d, 2H), 7.16(t, 2H), 5.44(s, 2H), 2.68(m, 2H), 2.15(s, 3H), 1.23(t, 3H).
Embodiment 2
[0024] o-Ethylacetophenone (45.00g, 0.30mol), 80% hydrazine hydrate (18.3ml, 0.30mol) and absolute ethanol (700ml) were mixed, stirred by magnetic force, and reacted at 25°C for 8 hours. After the reaction, add appropriate amount of distilled water, extract with ethyl acetate, wash with saturated brine, anhydrous Na 2 SO 4 Drying and rotary evaporation gave white crystal II (40.1 g, yield 82.4%).
Embodiment 3
[0026] o-Ethylacetophenone (29.6g, 0.20mol), 80% hydrazine hydrate (244ml, 4mol) and absolute ethanol (400ml) were mixed, stirred by magnetic force, and reacted at 100°C for 3 hours. After the reaction, add appropriate amount of distilled water, extract with ethyl acetate, wash with saturated brine, anhydrous Na 2 SO 4 Drying and rotary evaporation gave white crystal II (27.7 g, yield 85.4%).
[0027] Compound formula (I)
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Abstract
The invention provides a preparation method of an intermediate diethylbenzene. The preparation method comprises the steps: reacting diethyl acetophenone and hydrazine hydrate, and making a compound react with alkaline to obtain the diethylbenzene. The preparation method provided by the invention has the advantages of availability of raw materials, simplicity and convenience in operation, good quality, high yield and low cost, and is suitable for large-scale industrialized production.
Description
technical field [0001] The present invention relates to a new method for preparing o-diethylbenzene. Background technique [0002] Indacaterol, chemical name is (R)-5-[2-(5,6-diethylindan-2-amino)-1-hydroxyethyl]-8-hydroxy-1H-quinoline-2 -Ketomaleate, a new type of ultra-long-acting beta 2 Receptor agonist is a new inhaled drug for chronic obstructive pulmonary disease (COPD), with rapid onset and long-lasting bronchodilation effect. It only needs to be taken once a day to significantly improve the patient's lung function and wheezing symptoms, and is safe. and well tolerated, it was first approved for marketing in the European Union in November 2009. [0003] [0004] O-diethylbenzene is one of the important intermediates, and its structure is shown in formula (I): [0005] [0006] In the prior art, Journal of the American Chemical Society, 1992, vol.114(8), p.3123-3125 describes the synthesis method of (I), using 1,2-divinylbenzene hydrogenation, the yield is onl...
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