CN105646324B - 一种高纯度吲哚的制备方法 - Google Patents
一种高纯度吲哚的制备方法 Download PDFInfo
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- 150000002475 indoles Chemical class 0.000 title claims abstract description 55
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 16
- 239000011734 sodium Substances 0.000 claims abstract description 16
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims abstract description 13
- ZFRKQXVRDFCRJG-UHFFFAOYSA-N skatole Chemical compound C1=CC=C2C(C)=CNC2=C1 ZFRKQXVRDFCRJG-UHFFFAOYSA-N 0.000 claims abstract description 13
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims abstract description 13
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims abstract description 13
- 239000012535 impurity Substances 0.000 claims abstract description 10
- 229940079827 sodium hydrogen sulfite Drugs 0.000 claims abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 235000019441 ethanol Nutrition 0.000 claims description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- 239000012043 crude product Substances 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 3
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- 235000011121 sodium hydroxide Nutrition 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 9
- 238000005406 washing Methods 0.000 abstract description 6
- 238000005904 alkaline hydrolysis reaction Methods 0.000 abstract description 5
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- 239000000463 material Substances 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 239000012429 reaction media Substances 0.000 abstract description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 239000012065 filter cake Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000003814 drug Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical group NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000011280 coal tar Substances 0.000 description 2
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- 239000012847 fine chemical Substances 0.000 description 2
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- 238000004519 manufacturing process Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 2
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- 238000000746 purification Methods 0.000 description 2
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 2
- 229910001948 sodium oxide Inorganic materials 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- BNGXYYYYKUGPPF-UHFFFAOYSA-M (3-methylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].CC1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BNGXYYYYKUGPPF-UHFFFAOYSA-M 0.000 description 1
- RRTQTOBOLIGMED-UHFFFAOYSA-N 2-(carboxyamino)-2-phenylacetic acid Chemical group OC(=O)NC(C(O)=O)C1=CC=CC=C1 RRTQTOBOLIGMED-UHFFFAOYSA-N 0.000 description 1
- AMXMODDEDUGKDR-UHFFFAOYSA-N 3-hydroxy-1h-indole-2-carboxylic acid Chemical compound C1=CC=C2C(O)=C(C(=O)O)NC2=C1 AMXMODDEDUGKDR-UHFFFAOYSA-N 0.000 description 1
- CGWWRMKUJFUTPT-UHFFFAOYSA-N 3-methyl-1h-indole Chemical compound C1=CC=C2C(C)=CNC2=C1.C1=CC=C2C(C)=CNC2=C1 CGWWRMKUJFUTPT-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001062009 Indigofera Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000012803 melt mixture Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229940074386 skatole Drugs 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Abstract
本发明涉及一种高纯度吲哚的制备方法,属于有机合成技术领域。其是以吲哚为原料,经过与亚硫酸氢钠加成反应,得到2‑磺酸钠吲哚啉,溶剂洗涤去除杂质,然后加碱水解制得高纯度吲哚。主要特征在于反应过程中吲哚中含有的主要杂质3‑甲基吲哚不与亚硫酸氢钠发生反应,而达到吲哚与3‑甲基吲哚的分离目的。本发明在加成反应和水解反应中都使用水为反应介质,溶剂可回收套用,原料成本低,收率高。
Description
技术领域
本发明属于有机合成技术领域,涉及一种高纯度吲哚的制备方法。
背景技术
吲哚是一种重要的医药、农药中间体,广泛应用于医药、农药、染料等精细化学品的生产。吲哚在很低的浓度下,吲哚具有类似于花的香味,是许多花香的组成部分,广泛用于配制各种香精。
吲哚类化合物具有一系列生物活性。也是一类重要的精细化工产品,广泛用作有机、染料、医药和医药中间体,其许多衍生物具有显著的药理活性。在临床医药上,其中一些吲哚衍生物已用来治疗多种疾病,如癌症、肿瘤、艾滋病、消炎镇痛以及病毒性疾病和传染性疾病。
吲哚有很多生产方法。
1.从洗油馏分提取
在高温煤焦油中,约含吲哚0.10-0.16%。一般可从煤焦油和洗油馏分提取。将洗油馏分经碱洗、酸洗,得到甲基萘馏分,然后在60块理论板的高效塔中精馏,切取出225-256℃馏分段,加氢氧化钾熔融。反应在170-240℃进行2-4h,搅拌至停止冒泡为止。静置,把下层吲哚钾放出冷却,打碎后在低温下用苯洗涤除油。然后在50-70℃进行水解得到粗吲哚油,将其在20块理论板的蒸馏塔内蒸馏,取回流比8-10:1,切取塔顶温度170-256℃馏分,冷却,结晶、离心过滤,即得精制吲哚。再经过压榨,使含油量在3%以下,用乙醇重结晶,得纯度为99%的精制吲哚。
2.由邻氨基乙苯催化脱氢制得
邻氨基乙苯在氮气流中,在硝酸铝(或三氧化二铝)存在下,在550℃脱氢环化,经减压蒸馏得到二氢吲哚。再在640℃脱氢,得到吲哚。其他的制法还有由邻硝基甲苯和草酸酯反应,生成邻硝基苯基丙酮酸然后再制成α-吲哚羧酸,最后与石灰一起干馏而得产品;将苯胺与乙炔在600-650℃加热合成吲哚;将邻羧基苯基甘氨酸经3-羟基-2-吲哚羧酸和吲哚酸而合成吲哚;以浓硝酸或铬酸氧化静蓝得到吲哚醌,后者与锌粉进行蒸馏可得吲哚。将混合硝基肉桂酸与10份氢氧化钾粉末,加铁屑后加热将混合物熔化也可得到吲哚。
吲哚目前主要的合成方法:邻甲苯胺加甲酸生成N-甲酰基邻甲苯胺和水,N-甲酰基邻甲苯胺加入氢氧化钾在高温下环合后生成吲哚,最后采用水蒸汽蒸馏,冷却,过滤,得到吲哚。
但是,无论是提取吲哚,还是合成吲哚,都或多或少含有主要杂质3-甲基吲哚,3-甲基吲哚(3-methylindole)有粪臭,又名粪臭素(skatole),浓度高时的气息令人作呕,严重影响吲哚品质。
在实际使用过程中需要高纯度吲哚,含量≥99.5%,甚至99.9%,3-甲基吲哚≤0.5%,甚至0.1%以下。
由于3-甲基吲哚与吲哚物理化学性质非常相似,一般的物理分离方法如精馏重结晶方法很难把它们彻底分开,本发明的原理是巧妙利用反应过程中吲哚中含有的主要杂质3-甲基吲哚不与亚硫酸氢钠发生反应,而达到吲哚与3-甲基吲哚的分离目的。可以得到含量≥99.5%,甚至99.9%以上的高纯度吲哚。
发明内容
一种高纯度吲哚的制备方法,包括以下步骤:
(1)合成2-磺酸钠吲哚啉:将吲哚粗品溶解于醇类有机溶剂中,加入亚硫酸氢钠或亚硫酸氢钾水溶液后于20~30℃反应15-30h,反应结束后反应液经过滤、洗涤、干燥得中间体2-磺酸钠吲哚啉;
(2)水解:中间体2-磺酸钠吲哚啉再加入氢氧化钠或氢氧化钾水溶液回流12-20h,反应液冷却析晶,经过滤、洗涤、干燥得高纯度吲哚产品。
其中,步骤(1)中所述亚硫酸氢钠或亚硫酸氢钾水溶液,质量浓度为20~30%,添加量为吲哚质量的6~10倍。
步骤(1)中醇类有机溶剂为甲醇、乙醇、和异丙醇中的至少一种;醇类有机溶剂添加量吲哚重量的1~5倍。
步骤(2)中氢氧化钠或氢氧化钾水溶液的质量浓度为5~15%,添加量为中间体2-磺酸钠吲哚啉质量的3~5倍。
步骤(1)中吲哚粗品中含有的杂质不仅仅限制于3-甲基吲哚,也适用于其他不与亚硫酸氢钠发生反应的杂质。
本发明是以吲哚为原料,经过与亚硫酸氢钠加成反应,得到2-磺酸钠吲哚啉,溶剂洗涤去除杂质,然后加碱水解制得高纯度吲哚。在反应过程中吲哚中含有的主要杂质3-甲基吲哚不与亚硫酸氢钠发生反应,而达到吲哚与3-甲基吲哚的分离目的。本发明在加成反应和水解反应中都使用水为反应介质,溶剂可回收套用,原料成本低,收率高。
具体实施方式
实施例1
一种高纯度吲哚的制备方法,包括以下步骤:
(1)合成2-磺酸钠吲哚啉:向2000L反应釜中抽入250kg乙醇,开搅拌,投入140kg吲哚粗品,搅拌溶解。开始滴加20%的亚硫酸氢钠溶液1400kg,控制滴加时间为2h。滴加完毕后30℃保温20h。反应完毕后反应液经抽滤、乙醇洗涤,得大约300kg中间体2-磺酸钠吲哚啉。
(2)水解:将滤饼转入碱解釜(滤饼大约300kg),加水1000L搅拌,然后分批加入氢氧化钠100kg,升温蒸出乙醇,内温95℃以上,保持少量回流20h。降温至20℃,抽滤离心,用水洗涤滤饼。得到高纯度吲哚大约125kg。
实施例2
一种高纯度吲哚的制备方法,包括以下步骤:
(1)合成2-磺酸钠吲哚啉:向2000L反应釜中抽入700kg甲醇,开搅拌,投入140kg吲哚,搅拌溶解。开始滴加23%的亚硫酸氢钾溶液840kg,控制滴加时间为3h。滴加完毕后35℃保温20h。反应完毕后反应液经抽滤、甲醇洗涤,得大约300kg中间体2-磺酸钠吲哚啉。
(2)水解:将滤饼转入碱解釜(滤饼大约300kg),加水1000L搅拌,然后分批加入氢氧化钾100kg,升温蒸出甲醇,内温95℃以上,保持少量回流20h。降温至20℃,抽滤离心,用水洗涤滤饼。得到高纯度吲哚大约120kg。
实施例3
一种高纯度吲哚的制备方法,包括以下步骤:
(1)合成2-磺酸钠吲哚啉:向2000L反应釜中抽入250kg乙醇,开搅拌,投入140kg吲哚粗品,搅拌溶解。开始滴加30%的亚硫酸氢钠溶液900kg,控制滴加时间为2h。滴加完毕后30℃保温20h。反应完毕后反应液经抽滤、乙醇洗涤,得大约290kg中间体2-磺酸钠吲哚啉。
(2)水解:将滤饼转入碱解釜(滤饼大约290kg),加水1000L搅拌,然后分批加入氢氧化钠100kg,升温蒸出乙醇,内温95℃以上,保持少量回流20小时。降温至20℃,抽滤离心,用水洗涤滤饼。得到高纯度吲哚大约118kg。
Claims (1)
1.一种吲哚的制备方法,其特征在于,包括以下步骤:
(1)合成2-磺酸钠吲哚啉:将吲哚粗品溶解于醇类有机溶剂中,加入亚硫酸氢钠水溶液后于20~30℃反应15-30h,反应结束后反应液经过滤、洗涤、干燥得中间体2-磺酸钠吲哚啉;
(2)水解:中间体2-磺酸钠吲哚啉再加入氢氧化钠水溶液回流12-20h,反应液冷却析晶,经过滤、洗涤、干燥得吲哚产品;
所述步骤(1)中所述亚硫酸氢钠水溶液,质量浓度为20~30%,添加量为吲哚质量的6~10倍;
所述步骤(1)中醇类有机溶剂为甲醇、乙醇、和异丙醇中的至少一种;醇类有机溶剂添加量为吲哚重量的1~5倍;
所述步骤(2)中氢氧化钠水溶液的质量浓度为5~15%,添加量为中间体2-磺酸钠吲哚啉质量的3~5倍;
所述步骤(1)中吲哚粗品中含有的杂质为3-甲基吲哚和或其他不与亚硫酸氢钠发生反应的杂质。
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Denomination of invention: A method for preparing high-purity indole Granted publication date: 20190416 Pledgee: Rudong sub branch of Bank of China Ltd. Pledgor: NANTONG WANNIANCHANG PHARMACEUTICAL Co.,Ltd. Registration number: Y2024980026380 |