CN106496144A - Synthesis process of afloquanone - Google Patents

Synthesis process of afloquanone Download PDF

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CN106496144A
CN106496144A CN 201610794035 CN201610794035A CN106496144A CN 106496144 A CN106496144 A CN 106496144A CN 201610794035 CN201610794035 CN 201610794035 CN 201610794035 A CN201610794035 A CN 201610794035A CN 106496144 A CN106496144 A CN 106496144A
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afloquanone
preparation
catalyst
process
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CN 201610794035
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Chinese (zh)
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方存杰
孙延标
方从彬
孙明哲
赵冬生
徐奎
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安徽省润生医药股份有限公司
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Abstract

The invention relates to the technical field of drug chemical production, and in particular, relates to a synthesis process of afloquanone. A bimetallic composite catalyst is adopted in the preparation process of the afloquanone, catalytic hydrogenation is performed at low pressure, and the yield and the reaction selectivity are effectively improved. The invention also relates to the preparation method of the afloquanone; 6-nitro-2-(fluoromethyl)-3-(2-methylphenyl)-4-(3H)-1,3-phthalazinone is used as a substrate, a catalyst used for preparation of the afloquanone and mentioned above is used as a catalyst, and the afloquanone is prepared by reduction, filtration, pH value regulation and recrystallization. The preparation method has strong chemical selectivity and is consistent with the concept of 'green chemistry', and moreover, the prepared product has high purity and wide application prospect.

Description

一种氟喹酮的合成工艺 A fluoropolymer synthesis of methaqualone

技术领域 FIELD

[0001] 本发明涉及药物化学生产技术领域,具体涉及一种氟喹酮的合成工艺。 [0001] Technical Field The present invention relates to the production of pharmaceutical chemistry, specifically relates to a process for the synthesis of fluoro-quinolin-one.

背景技术 Background technique

[0002] 氟喹酮是一种肌肉松弛药,药物作用于脊髓上位中枢较广泛的部位,进而缓解肌肉紧张性亢进状态。 [0002] fluoro-quinolin-one is a muscle relaxant, a drug acting on the central spinal broader upper portion, and thus relieve muscle tension state hyperthyroidism. 氟喹酮是一个对面、颈部肌肉痉挛有良好疗效的松弛剂,已经经过二十多年的临床应用,且取得很好的医疗效果,如应用于以下症状:脑血管障碍、脑性麻痹、痉挛性脊髓麻痹、脊髓血管障碍、后纵韧带骨化症、多发性硬化症、肌萎缩性侧索硬化症、脊髓小脑变性症、外伤后遗症(脊髓损伤、头部外伤)、术后后遗症(包括脑、脊髓肿瘤)及其它脑脊髓疾患引起的痉挛性麻痹。 Opposite it is a fluoroquinolone ketones, neck muscle spasms have a good effect relaxant, has over twenty years of clinical application, and achieved very good health effects, such as used in the following symptoms: cerebrovascular disorder, cerebral palsy, spastic spinal paralysis, spinal vascular disorder, ossification of posterior longitudinal ligament, multiple sclerosis, amyotrophic lateral sclerosis, spinocerebellar degeneration, traumatic sequelae (spinal cord injury, head injury), postoperative complications (including brain and spinal cord tumors), and other spastic paralysis caused by cerebrospinal disease.

[0003] 因为氟喹酮结构中含有多个容易被氢化的部位,所以,在以前研究中加氢还原这一步会产生大量的其他还原产物,如:A、B和C这三种副产物。 [0003] Because the structure contains fluorine methaqualone plurality readily hydrogenated site, therefore, in the previous studies hydrogenation step which will produce a lot of other reduction products, such as: A, B, and C of the three-product.

[0004] [0004]

Figure CN106496144AD00031

发明内容 SUMMARY

[0005] 本发明针对现有中氟喹的制备过程中,产物纯度低及化学选择性差的缺点,公开了一种氟喹酮的合成工艺;合成过程中化学选择性强,制备方便,条件简单,安全可靠,适合工业化生产。 [0005] The present invention is directed to the preparation process of the prior-fluoro-quinoline, product purity, and low chemical selectivity shortcomings, discloses a process for the synthesis of fluoro-quinolin-one; chemical synthesis selectivity, easy preparation, simple condition , safe and reliable, suitable for industrial production.

[0006] 为实现以上目的,本发明通过以下技术方案予以实现: [0006] To achieve the above object, the present invention is realized by the following technical solutions:

[0007] 一种氟喹酮的合成工艺,包括如下步骤: [0007] A-fluoro-quinolin-one process, comprising the steps of:

[0008] A.向氢化装置中加入6-硝基-2-(氟甲基)-3- (2-甲基苯基)-4- (3H) -1,3-二氮杂萘酮、催化加氢溶剂和催化剂,氢气压力为〇. 02~0.4MPa,温度为25-50°C反应,反应0.5-1.5小时后,过滤得滤液; [0008] A. 6-Nitro added to a hydrogenation apparatus 2- (fluoromethyl) -3- (2-methylphenyl) -4- (3H) -1,3- phthalazinone, catalytic hydrogenation catalyst and a solvent, a hydrogen pressure of square 02 ~ 0.4MPa, reaction temperature of 25-50 ° C, after the reaction 0.5 to 1.5 hours, filtered to obtain a filtrate.;

[0009] B.用乙醇洗涤催化剂,常温条件下,减压得到溶液(I); [0009] B. the catalyst was washed with ethanol, normal temperature under reduced pressure to obtain a solution (the I);

[0010] C.向滤液和溶液⑴中加入水,加入0.1N氢氧化钠溶液,调节pH至10.2~11.0,在50-60 °C搅拌0.5-1小时,冷却至室温,过滤得氟喹酮粗品; [0010] C. was added to the filtrate and the solution ⑴ water, 0.1N sodium hydroxide solution was added, the pH adjusted to 10.2 to 11.0, and stirred at 50-60 ° C 0.5-1 hours, cooled to room temperature and filtered to give fluoro-quinolin-one Crude;

[0011] D.每克氟喹酮粗品中加入5~15ml的重结晶溶剂,常温下进行结晶,过滤得到氟喹酮; [0011] D.-fluoro-quinolin added per gram of crude ketone was recrystallized from 5 ~ 15ml of the solvent, crystallization at room temperature, and filtered to give fluoro-quinolin-one;

[0012] 所述步骤A中,每克6-硝基-2-(氟甲基)-3- (2-甲基苯基)-4- (3H) -1,3-二氮杂萘酮中加入催化加氢溶剂的体积为12~16ml; [0012] Step A per g of 6-nitro-2- (fluoromethyl) -3- (2-methylphenyl) -4- (3H) -1,3- phthalazinone volume was added catalytic hydrogenation solvent is 12 ~ 16ml;

[0013] 步骤A中,催化加氢溶剂为含酸量为0.1~0.4N的含酸的醇溶液; [0013] Step A, the catalytic hydrogenation solvent is an acid alcohol solution in an amount of 0.1 ~ 0.4N of the acid-containing;

[0014] 步骤d中,重结晶溶剂包括醇溶液(m)、酯溶液(ii)和水;醇溶液(m)为ci~C4的醇溶液,酯溶液(II)为C1~C6的酯溶液;醇溶液(m)、酯溶液(II)和水的体积比为1:0.2~ 1:0.2 ~1〇 [0014] Step d, the recrystallization solvent comprises an alcohol solution of (m), ester solution (ii) and water; alcohol solution (m) is an alcohol solution ci ~ C4, the ester solution (II) is an ester solution of C1 ~ C6 of ; alcohol solution (m), a solution of the ester (II) and a volume ratio of water is 1: 0.2 to 1: 0.2 to 1〇

[0015] 优选的,所述催化剂为钌钯双金属催化剂。 [0015] Preferably, the palladium catalyst is a ruthenium bimetallic catalyst.

[0016] 优选的,所述催化剂与6-硝基-2-(氟甲基)-3- (2-甲基苯基)-4- (3H) -1,3-二氮杂萘酮的质量比为1:5~20。 [0016] Preferably, the catalyst with 6-nitro-2- (fluoromethyl) -3- (2-methylphenyl) -4- (3H) -1,3- naphthyridine-one mass ratio of 1: 5 to 20.

[0017] 优选的,所述含酸的醇溶液包括酸溶液和醇溶液(I),酸溶液为硫酸或盐酸或冰醋酸;醇溶液⑴为甲醇、乙醇、正丁醇中的其中一种。 [0017] Preferably, the acid-containing alcohol solution comprises an acid solution and an alcohol solution (the I), or a hydrochloric acid solution is sulfuric acid or acetic acid; ⑴ alcoholic solution is methanol, ethanol, n-butanol one.

[0018] 优选的,所述含酸的醇-酯混合溶液包括酸溶液、醇溶液(II)和酯溶液(I);酸溶液为硫酸或盐酸或冰醋酸;醇溶液(II)为甲醇、乙醇、正丁醇中的其中一种;酯溶液(I)为醋酸乙酯或甲酸丁酯。 [0018] Preferably, the acid-containing alcohol - ester solution comprises a mixed acid solution, an alcohol solution (II) and the ester solution (the I); or a hydrochloric acid solution is sulfuric acid or acetic acid; alcohol solution (II) is methanol, ethanol, n-butanol one; ester solution (I) is ethyl acetate or butyl.

[0019] 优选的,所述醇溶液(m)为甲醇、乙醇、异丙醇中一种或两种以上;酯溶液(II)为醋酸乙酯或甲酸丁酯。 [0019] Preferably, the alcohol solution of (m) is methanol, ethanol, isopropanol or two or more; ester solution (II) is ethyl acetate or butyl.

[0020] 本发明的有益效果为: [0020] Advantageous effects of the present invention are:

[0021] (1)本发明采用了双金属复合催化剂,在低压进行催化加氢,有效的提高了收率, 产率能够达到90%以上,最高可以达到96.9%。 [0021] (1) The present invention employs a composite bimetallic catalysts, catalytic hydrogenation at low pressure, effectively increasing the yield, the yield can reach 90% or more, up to the 96.9%.

[0022] (2)本发明采用了双金属复合催化剂,在低压进行催化加氢,有效的抑制氢化副产物A、B和C的生成,大大提高了反应的选择性。 [0022] (2) The present invention employs a composite bimetallic catalysts, catalytic hydrogenation at low pressure, effectively inhibit the formation of hydrogenated by-products A, B and C, which greatly improves the selectivity of the reaction.

[0023] (3)本发明氟喹酮的制备方法,操作简单、环保、经济、高效、无毒,符合"绿色化学" 理念,具有广阔的工业应用前景。 [0023] (3) Preparation of a fluorine methaqualone the present invention, the operation is simple, environmentally friendly, economical, effective, non-toxic, "green chemistry" concept has broad industrial application.

[0024] ⑷本发明提供了一种氟喹酮简单的精制方法,提高了产品的纯度,减少了杂质的含量,符合国标的要求。 [0024] ⑷ present invention provides a simple one-fluoro-quinolin purification methods to improve the purity of the product, reducing the content of impurities, consistent with national standard requirements.

具体实施方式 detailed description

[0025] 为使本发明实施例的目的、技术方案和优点更加清楚,下面将结合本发明的实施例,对本发明实施例中的技术方案进行清楚、完整地描述。 [0025] The object of the present invention, technical solutions, and advantages of the embodiments more clearly below with reference to examples of the present invention, the technical solutions of the present invention in embodiments will be clearly and completely described. 基于本发明中的实施例,本领域普通技术人员在没有作出创造性劳动前提下所获得的所有其他实施例,都属于本发明保护的范围。 Based on the embodiments of the present invention, those of ordinary skill in the art to make all other embodiments without creative work obtained by, it falls within the scope of the present invention.

[0026] 实施例1: [0026] Example 1:

[0027] 一种氟喹酮的合成工艺,包括如下步骤: [0027] A-fluoro-quinolin-one process, comprising the steps of:

[0028] A.向氢化装置中加入10g 6-硝基-2-(氟甲基)-3-(2-甲基苯基)-4-(3H)-1,3-二氮杂萘酮、150ml含酸量为0.1~0.4N的冰醋酸正丁醇溶液,lg钌钯双金属催化剂,氢气压力为0.02~0.4MPa,温度为25-50°C反应,反应1小时后,过滤得滤液; [0028] A. To the hydrogenation apparatus 10g 6- nitro-2- (fluoromethyl) -3- (2-methylphenyl) -4- (3H) -1,3- phthalazinone , 150ml acid content of 0.1 ~ 0.4N n-butanol solution of acetic acid, lg palladium ruthenium bimetallic catalyst, hydrogen pressure 0.02 ~ 0.4MPa, reaction temperature of 25-50 ° C, after 1 hour, filtered to give the filtrate ;

[0029] B.用乙醇洗涤催化剂,常温条件下,减压得到溶液⑴; [0029] B. washed catalyst with ethanol, at normal temperature, under reduced pressure to obtain a solution ⑴;

[0030] C.向滤液和溶液⑴中加入水,加入0.1N氢氧化钠溶液,调节pH至10.2~11.0,在50-60 °C搅拌0.5小时,冷却至室温,过滤得氟喹酮粗品; [0030] C. was added to the filtrate and the solution ⑴ water, 0.1N sodium hydroxide solution was added, the pH adjusted to 10.2 to 11.0, and stirred at 50-60 ° C 0.5 h, cooled to room temperature and filtered to give the crude fluoro-quinolin-one;

[0031] D.每克氟喹酮粗品中加入5~15ml的重结晶溶剂,其中,重结晶溶剂为体积比为1: 1:0.2的异丙醇溶液(m)、甲酸丁酯溶液(II)和水的混合液;常温下进行结晶,过滤得到氟喹酮。 [0031] D.-fluoro-quinolin per gram of the recrystallization solvent was added 5 ~ 15ml crude ketone, wherein the recrystallization solvent is a volume ratio of 1: 1: 0.2 in a solution of isopropanol (m), a solution of acid butyl ester (II ) and water mixture; crystallized at room temperature, filtered to give a fluorine methaqualone.

[0032] 实施例2: [0032] Example 2:

[0033] 一种氟喹酮的合成工艺,包括如下步骤: [0033] A-fluoro-quinolin-one process, comprising the steps of:

[0034] A.向氢化装置中加20g 6-硝基_2_(氟甲基)-3-(2_甲基苯基)-4-(3扣-1,3-二氮杂萘酮、240ml含酸量为0.1~0.4N的含酸的盐酸乙醇溶液,lg钌钯双金属催化剂,氢气压力为0.02~0.4MPa,温度为25-50°C反应,反应0.5小时后,过滤得滤液; [0034] A. hydrogenation apparatus added to 20g 6- nitro _2_ (fluoromethyl) -3- (2_-methylphenyl) -4- (3-1,3-phthalazinone buckle, acid content of the acid-containing 240ml 0.1 ~ 0.4N ethanol solution of hydrochloric acid, lg palladium ruthenium bimetallic catalyst, hydrogen pressure 0.02 ~ 0.4MPa, reaction temperature of 25-50 ° C. after 0.5 hours the reaction was filtered to obtain filtrate;

[0035] B.用乙醇洗涤催化剂,常温条件下,减压得到溶液⑴; [0035] B. washed catalyst with ethanol, at normal temperature, under reduced pressure to obtain a solution ⑴;

[0036] C.向滤液和溶液⑴中加入水,加入0.1N氢氧化钠溶液,调节pH至10.2~11.0,在50-60°C搅拌1小时,冷却至室温,过滤得氟喹酮粗品; [0036] C. was added to the filtrate and the solution ⑴ water, 0.1N sodium hydroxide solution was added, the pH adjusted to 10.2 to 11.0, and stirred at 50-60 ° C 1 hour, cooled to room temperature and filtered to give the crude fluoro-quinolin-one;

[0037] D.每克氟喹酮粗品中加入5~15ml的重结晶溶剂,其中,重结晶溶剂为体积比为1: o.2:i的甲醇溶液(m)、醋酸乙酯溶液(II)和水的混合液;常温下进行结晶,过滤得到氟喹酮。 [0037] D.-fluoro-quinolin added per gram of crude ketone was recrystallized from 5 ~ 15ml of the solvent, wherein the recrystallization solvent is a volume ratio of 1: o.2: methanol solution of i (m), an ethyl acetate solution (II ) and water mixture; crystallized at room temperature, filtered to give a fluorine methaqualone.

[0038] 实施例3: [0038] Example 3:

[0039] -种氟喹酮的合成工艺,包括如下步骤: [0039] - quinolin-fluoro-one kind of process, comprising the steps of:

[0040] A.向氢化装置中加入5g 6-硝基_2_(氟甲基)-3-(2-甲基苯基)-4-(3珀-1,3-二氮杂萘酮、80ml含酸量为0.1~0.4N的硫酸甲醇溶液,lg钌钯双金属催化剂,氢气压力为0.02 ~0.4MPa,温度为25-50°C反应,反应1.5小时后,过滤得滤液; [0040] A. Add 5g 6- nitro apparatus _2_ hydride (fluoromethyl) -3- (2-methylphenyl) -4- (3-1,3-Perot phthalazinone, 80ml methanol containing an acid in an amount of 0.1 ~ 0.4N solution of sulfuric acid, lg palladium ruthenium bimetallic catalyst, hydrogen pressure 0.02 ~ 0.4MPa, reaction temperature of 25-50 ° C. after 1.5 hours the reaction was filtered to obtain filtrate;

[0041] B.用乙醇洗涤催化剂,常温条件下,减压得到溶液(I); [0041] B. the catalyst was washed with ethanol, normal temperature under reduced pressure to obtain a solution (the I);

[0042] C.向滤液和溶液(I)中加入水,加入0.1N氢氧化钠溶液,调节pH至10.2~11.0,在50-60°C搅拌1小时,冷却至室温,过滤得氟喹酮粗品; [0042] C. was added to the filtrate and the solution (I) water, 0.1N sodium hydroxide solution was added, the pH adjusted to 10.2 to 11.0, and stirred at 50-60 ° C 1 hour, cooled to room temperature and filtered to give fluoro-quinolin-one Crude;

[0043] D.每克氟喹酮粗品中加入5~15ml的重结晶溶剂,其中,重结晶溶剂为体积比为1: 0.2:0.2的乙醇溶液(m)、甲酸丁酯溶液(II)和水的混合液;常温下进行结晶,过滤得到氟喹酮。 [0043] D. methaqualone fluorine per gram of crude product were added 5 ~ 15ml recrystallization solvent, wherein the recrystallization solvent is a volume ratio of 1: 0.2: 0.2 ethanol solution (m), carboxylic acid butyl ester (II) and water mixture; crystallization at room temperature, and filtered to give fluoro-quinolin-one.

[0044] 以上实施例仅用以说明本发明的技术方案,而非对其限制;尽管参照前述实施例对本发明进行了详细的说明,本领域的普通技术人员应当理解:其依然可以对前述各实施例所记载的技术方案进行修改,或者对其中部分技术特征进行等同替换;而这些修改或者替换,并不使相应技术方案的本质脱离本发明各实施例技术方案的精神和范围。 [0044] The above embodiments are intended to illustrate the present invention, rather than limiting;. Although the present invention has been described in detail embodiments, those of ordinary skill in the art should be understood: each of the foregoing which still the technical solutions described in the embodiments may be modified, or some technical features equivalents; as such modifications or replacements do not cause the essence of corresponding technical solutions to depart from the spirit and scope of the technical solutions of the embodiments of the present invention.

Claims (6)

  1. 1. 一种氟喹酮的合成工艺,其特征在于,包括如下步骤: A. 向氢化装置中加入6-硝基-2-(氟甲基)-3- (2-甲基苯基)-4- (3H) -1,3_二氮杂萘酮、 催化加氢溶剂和催化剂,氢气压力为0.02~0.4MPa,温度为25-50 °C反应,反应0.5-1.5小时后,过滤得滤液; B. 用乙醇洗涤催化剂,常温条件下,减压得到溶液(I); C. 向滤液和溶液⑴中加入水,加入0.1N氢氧化钠溶液,调节pH至10.2~11.0,在50-60 °C搅拌0.5-1小时,冷却至室温,过滤得氟喹酮粗品; D. 每克氟喹酮粗品中加入5~15ml的重结晶溶剂,常温下进行结晶,过滤得到氟喹酮; 所述步骤A中,每克6-硝基-2-(氟甲基)-3- (2-甲基苯基)-4- (3H) -1,3-二氮杂萘酮中加入催化加氢溶剂的体积为12~16ml; 步骤A中,催化加氢溶剂为含酸量为0.1~0.4N的含酸的醇溶液; 步骤D中,重结晶溶剂包括醇溶液(m)、酯溶液(II)和水;醇溶液(m)为C1~C4的醇溶液, A fluorine-quinolin-one process, characterized by comprising the steps of: A. added to a hydrogenation apparatus 6-nitro-2- (fluoromethyl) -3- (2-methylphenyl) - 4- (3H) -1,3_ phthalazinone, catalytic hydrogenation solvent and a catalyst, hydrogen pressure 0.02 ~ 0.4MPa, reaction temperature of 25-50 ° C, after the reaction 0.5 to 1.5 hours, filtered to give the filtrate ; B. catalyst was washed with ethanol, at normal temperature, under reduced pressure to obtain a solution (I); C. water was added to the filtrate and the solution ⑴ added 0.1N sodium hydroxide solution, adjusted to pH 10.2 to 11.0, in 50-60 ° C stirred for 0.5-1 hours, cooled to room temperature and filtered to give crude fluoro-quinolin-one; D. fluorine per gram of crude product was added methaqualone recrystallization solvent is 5 ~ 15ml, crystallization at room temperature, and filtered to give fluoro-quinolin-one; the step A per g of 6-nitro-2- (fluoromethyl) -3- (2-methylphenyl) -4- (3H) -1,3- phthalazinone was added catalytic hydrogenation the volume of solvent is 12 ~ 16ml; step a, the catalytic hydrogenation solvent is an acid alcohol solution in an amount of 0.1 ~ 0.4N of the acid-containing; step D, recrystallization solvent comprises an alcohol solution of (m), a solution of the ester (II ) and water; alcohol solution (m) is an alcohol solution of C1 ~ C4, 溶液(II)为C1~C6的酯溶液;醇溶液(m)、酯溶液(II)和水的体积比为1:0.2~1:0.2 ~1 〇 Solution (II) is C1 ~ C6 of the ester solution; alcohol solution (m), a solution of the ester (II) and a volume ratio of water is 1: 0.2 to 1: 0.2 to 1 billion
  2. 2. 如权利要求1所述的氟喹酮的合成工艺,其特征在于,所述催化剂为钌钯双金属催化剂。 2-fluoro-quinolin-one process according to claim 1, wherein the ruthenium catalyst is a palladium bimetallic catalyst.
  3. 3. 如权利要求1所述的氟喹酮的合成工艺,其特征在于,所述催化剂与6-硝基-2-(氟甲基)-3- (2-甲基苯基)-4- (3H) -1,3-二氮杂萘酮的质量比为1:5~20。 3-fluoro-quinolin-one The process according to claim 1, characterized in that the catalyst with 6-nitro-2- (fluoromethyl) -3- (2-methylphenyl) -4- (3H) mass ratio of 1,3-diaza-tetralone is 1: 5 to 20.
  4. 4. 如权利要求1所述的氟喹酮的合成工艺,其特征在于,所述含酸的醇溶液包括酸溶液和醇溶液(I),酸溶液为硫酸或盐酸或冰醋酸;醇溶液(I)为甲醇、乙醇、正丁醇中的其中一种。 Alcohol solution (; 4-fluoro-quinoline as claimed in one of the synthetic process of claim 1 or a hydrochloric acid solution is sulfuric acid or acetic acid, characterized in that the acid-containing alcohol solution comprises an acid solution and an alcohol solution (the I), I) is methanol, ethanol, n-butanol one.
  5. 5. 如权利要求1所述的氟喹酮的合成工艺,其特征在于,所述含酸的醇-酯混合溶液包括酸溶液、醇溶液(II)和酯溶液(I);酸溶液为硫酸或盐酸或冰醋酸;醇溶液(II)为甲醇、乙醇、正丁醇中的其中一种;酯溶液(I)为醋酸乙酯或甲酸丁酯。 5-fluoro-quinolin-one process according to claim 1, wherein the acid-containing alcohol - ester solution comprises a mixed acid solution, an alcohol solution (II) and the ester solution (the I); for the sulfuric acid solution or hydrochloric acid or acetic acid; wherein an alcohol solution (II) is methanol, ethanol, n-butanol; ester solution (I) is ethyl acetate or butyl.
  6. 6. 如权利要求1所述的氟喹酮的合成工艺,其特征在于,所述醇溶液(ΙΠ )为甲醇、乙醇、 异丙醇中一种或两种以上;酯溶液(II)为醋酸乙酯或甲酸丁酯。 6-fluoro-quinolin-one process according to claim 1, wherein said alcohol solution (ΙΠ) methanol, ethanol, isopropanol or two or more; ester solution (II) is acetic acid ethyl or butyl.
CN 201610794035 2016-08-31 2016-08-31 Synthesis process of afloquanone CN106496144A (en)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103551144A (en) * 2013-11-22 2014-02-05 杭州杜易科技有限公司 Bimetallic composite catalyst for preparing afloqualone and method for preparing afloqualone
CN103613549A (en) * 2013-10-11 2014-03-05 浙江工业大学 Afloqualone preparation method

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103613549A (en) * 2013-10-11 2014-03-05 浙江工业大学 Afloqualone preparation method
CN103551144A (en) * 2013-11-22 2014-02-05 杭州杜易科技有限公司 Bimetallic composite catalyst for preparing afloqualone and method for preparing afloqualone

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