CN113773247A - 一种2-氨基-5-碘吡啶的制备方法 - Google Patents
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- IVILGUFRMDBUEQ-UHFFFAOYSA-N 5-iodopyridin-2-amine Chemical compound NC1=CC=C(I)C=N1 IVILGUFRMDBUEQ-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims abstract description 27
- 238000003756 stirring Methods 0.000 claims abstract description 23
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 239000008399 tap water Substances 0.000 claims abstract description 18
- 235000020679 tap water Nutrition 0.000 claims abstract description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000001914 filtration Methods 0.000 claims abstract description 15
- 238000004128 high performance liquid chromatography Methods 0.000 claims abstract description 14
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims abstract description 9
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims abstract description 9
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
- 238000001816 cooling Methods 0.000 claims abstract description 7
- 238000010438 heat treatment Methods 0.000 claims abstract description 7
- 239000002994 raw material Substances 0.000 claims abstract description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 48
- 239000012043 crude product Substances 0.000 claims description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- 238000005406 washing Methods 0.000 claims description 21
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- 238000007664 blowing Methods 0.000 claims description 14
- 238000001035 drying Methods 0.000 claims description 14
- 239000000706 filtrate Substances 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 10
- 239000000047 product Substances 0.000 claims description 10
- WGOLHUGPTDEKCF-UHFFFAOYSA-N 5-bromopyridin-2-amine Chemical compound NC1=CC=C(Br)C=N1 WGOLHUGPTDEKCF-UHFFFAOYSA-N 0.000 claims description 7
- 239000012065 filter cake Substances 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 7
- 239000012074 organic phase Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 2
- 239000007788 liquid Substances 0.000 abstract description 4
- 239000010815 organic waste Substances 0.000 abstract description 4
- 230000035484 reaction time Effects 0.000 abstract description 2
- 239000000758 substrate Substances 0.000 abstract description 2
- 238000001308 synthesis method Methods 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
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- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Abstract
一种2‑氨基‑5‑碘吡啶的制备方法,包括、将700‑800g的2‑氨基‑5‑溴吡啶、80‑85g碘化亚铜、1300‑1500g碘化钾、80‑90gN,N‑二甲基乙二胺和3600‑3800ml的DMF投入10L反应瓶中,搅拌,真空置换氮气,升温,T=100℃保温反应约5h,HPLC检测原料<5%。降温至T<40℃,加入自来水搅拌,过滤;该合成方法具有反应高效、快速,条件温和,底物简单易得、适用性较广,反应时间短、收率高等优点,路线设计合理,实验操作简单,易于实现,且得到的产物收率较高,而且不产生有机废液,反应过程安全无污染。
Description
技术领域
本发明涉及医药中间体的合成技术领域,具体为一种2-氨基-5-碘吡啶的制备方法。
背景技术
2-氨基-5-碘吡啶别名2-氨基-5-碘代吡啶,5-碘-2-氨基吡啶,CAS:20511-12-0,为有机合成的重要中间体,主要用于医药中间体,也用于染料生产,农药生产及香料等方面。
一般工艺是2-氨基吡啶在溶剂中与碘反应合成,收率约为83%,制备过程中生成有机废液,给环境带来压力。另一常用合成路线为以2-氨基-5-溴吡啶为原料,原料成本高且不易得,合成时仍有有机废液生成。
发明内容
(一)解决的技术问题
针对现有技术的不足,本发明提供了一种2-氨基-5-碘吡啶的制备方法
(二)技术方案
为实现上述目的,本发明提供如下技术方案:一种2-氨基-5-碘吡啶的制备方法,包括以下步骤:
步骤1、将700-800g的2-氨基-5-溴吡啶、80-85g 碘化亚铜、1300-1500g 碘化钾、80-90gN,N-二甲基乙二胺和3600-3800ml的DMF投入10L反应瓶中,搅拌,真空置换氮气,升温,T=100℃保温反应约5h, HPLC检测原料<5%。降温至T<40℃,加入自来水搅拌,过滤;
步骤2、滤饼用5L×3自来水洗涤,60℃鼓风干燥,得600-680g粗品1;滤液静置分层,水层用2L×2甲苯萃取,合并有机相,用3L水洗涤,60℃减压浓缩至干,得250g粗品2;
步骤3、粗品1及粗品2溶于6L甲醇,加入70-80g活性炭,室温搅拌,过滤,用1L热甲醇洗涤滤渣,合并滤液,减压浓缩至干,再60℃鼓风干燥,得700-750g产品。
本发明改进有,包括以下步骤:
步骤1、将750g2-氨基-5-溴吡啶、82.6g 碘化亚铜、1440g 碘化钾、83gN,N-二甲基乙二胺和3750ml DMF投入10L反应瓶中,搅拌,真空置换氮气,升温,T=100℃保温反应约5h,HPLC检测原料<5%。降温至T<40℃,加入自来水搅拌,过滤;
步骤2、滤饼用5L×3自来水洗涤,60℃鼓风干燥,得645g粗品;滤液静置分层,水层用2L×2甲苯萃取,合并有机相,用3L水洗涤,60℃减压浓缩至干,得粗品250g;
步骤3、645g+250g粗品溶于6L甲醇,加入75g活性炭,室温搅拌,过滤,用1L热甲醇洗涤滤渣,合并滤液,减压浓缩至干,再60℃鼓风干燥,得720g产品。
本发明改进有,所述步骤1中加入20L自来水搅拌0.5h。
本发明改进有,所述步骤3中室温搅拌1h。
(三)有益效果
与现有技术相比,本发明提供了一种2-氨基-5-碘吡啶的制备方法,具备以下有益效果:
新方法反应操作简单,通过简单的步骤就可以合成2-氨基-5-碘吡啶,该合成方法具有反应高效、快速,条件温和,底物简单易得、适用性较广,反应时间短、收率高等优点,路线设计合理,实验操作简单,易于实现,且得到的产物收率较高,而且不产生有机废液,反应过程安全无污染。
附图说明
图1为本发明的示意图。
具体实施方式
下面将结合本发明实施例中的附图,对本发明实施例中的技术方案进行清楚、完整地描述,显然,所描述的实施例仅仅是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域普通技术人员在没有做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。
实施例1
一种2-氨基-5-碘吡啶的制备方法,包括以下步骤:
步骤1、将700g的2-氨基-5-溴吡啶、80g 碘化亚铜、1300g 碘化钾、80gN,N-二甲基乙二胺和3600ml的DMF投入10L反应瓶中,搅拌,真空置换氮气,升温,T=100℃保温反应约5h, HPLC检测原料<5%。降温至T<40℃,加入自来水搅拌,过滤;
步骤2、滤饼用5L×3自来水洗涤,60℃鼓风干燥,得600-680g粗品1;滤液静置分层,水层用2L×2甲苯萃取,合并有机相,用3L水洗涤,60℃减压浓缩至干,得250g粗品2;
步骤3、粗品1及粗品2溶于6L甲醇,加入70g活性炭,室温搅拌,过滤,用1L热甲醇洗涤滤渣,合并滤液,减压浓缩至干,再60℃鼓风干燥,得700-750g产品。
实施例2
一种2-氨基-5-碘吡啶的制备方法,包括以下步骤:
将750g2-氨基-5-溴吡啶、82.6g 碘化亚铜、1440g 碘化钾、83gN,N-二甲基乙二胺和3750ml DMF投入10L反应瓶中,搅拌,真空置换氮气,升温,T=100℃保温反应约5h, HPLC检测原料<5%。降温至T<40℃,加入自来水搅拌,过滤;
步骤2、滤饼用5L×3自来水洗涤,60℃鼓风干燥,得645g粗品;滤液静置分层,水层用2L×2甲苯萃取,合并有机相,用3L水洗涤,60℃减压浓缩至干,得粗品250g;
步骤3、645g+250g粗品溶于6L甲醇,加入75g活性炭,室温搅拌,过滤,用1L热甲醇洗涤滤渣,合并滤液,减压浓缩至干,再60℃鼓风干燥,得720g产品。
实施例3
一种2-氨基-5-碘吡啶的制备方法,包括以下步骤:
步骤1、将800g的2-氨基-5-溴吡啶、85g 碘化亚铜、1500g 碘化钾、90gN,N-二甲基乙二胺和3800ml的DMF投入10L反应瓶中,搅拌,真空置换氮气,升温,T=100℃保温反应约5h, HPLC检测原料<5%。降温至T<40℃,加入自来水搅拌,过滤;
步骤2、滤饼用5L×3自来水洗涤,60℃鼓风干燥,得600-680g粗品1;滤液静置分层,水层用2L×2甲苯萃取,合并有机相,用3L水洗涤,60℃减压浓缩至干,得250g粗品2;
步骤3、粗品1及粗品2溶于6L甲醇,加入80g活性炭,室温搅拌,过滤,用1L热甲醇洗涤滤渣,合并滤液,减压浓缩至干,再60℃鼓风干燥,得700-750g产品。
本发明改进有,所述步骤1中加入20L自来水搅拌0.5h。
本发明改进有,所述步骤3中室温搅拌1h。
(HPLC条件: MeOH: 0.1%TFA =30: 70, 220nm),制备出的产品HPLC>90%。
具体的实施例2中的计量可以参照下表
物料 | 分子量 | 重量 | 摩尔数 | 摩尔比 | 备注 |
2-氨-5-溴吡啶 | 173.01 | 750g | 4.335 | 1.00 | |
碘化钾 | 166.00 | 1440g | 8.670 | 2.00 | |
碘化亚铜 | 190.45 | 82.6g | 0.434 | 0.10 | |
N,N-二甲基乙二胺 | 88.15 | 83.0g | 0.941 | 0.22 | |
甲醇 | 7.0L | 回收套用 | |||
活性炭 | 75g | ||||
DMF | 3750ml | ||||
甲苯 | 4L | 回收套用 | |||
2-氨基-5-碘吡啶 | 220.01 | 720g | 3.272 |
摩尔收率:75.5%
重量收率:96.0%
尽管已经示出和描述了本发明的实施例,对于本领域的普通技术人员而言,可以理解在不脱离本发明的原理和精神的情况下可以对这些实施例进行多种变化、修改、替换和变型,本发明的范围由所附权利要求及其等同物限定。
Claims (4)
1.一种2-氨基-5-碘吡啶的制备方法,其特征在于,包括以下步骤:
步骤1、将700-800g的2-氨基-5-溴吡啶、80-85g 碘化亚铜、1300-1500g 碘化钾、80-90gN,N-二甲基乙二胺和3600-3800ml的DMF投入10L反应瓶中,搅拌,真空置换氮气,升温,T=100℃保温反应约5h, HPLC检测原料<5%,降温至T<40℃,加入自来水搅拌,过滤;
步骤2、滤饼用5L×3自来水洗涤,60℃鼓风干燥,得600-680g粗品1;滤液静置分层,水层用2L×2甲苯萃取,合并有机相,用3L水洗涤,60℃减压浓缩至干,得250g粗品2;
步骤3、粗品1及粗品2溶于6L甲醇,加入70-80g活性炭,室温搅拌,过滤,用1L热甲醇洗涤滤渣,合并滤液,减压浓缩至干,再60℃鼓风干燥,得700-750g产品。
2.根据权利要求1所述的一种2-氨基-5-碘吡啶的制备方法,包括以下步骤:
步骤1、将750g2-氨基-5-溴吡啶、82.6g 碘化亚铜、1440g 碘化钾、83gN,N-二甲基乙二胺和3750ml DMF投入10L反应瓶中,搅拌,真空置换氮气,升温,T=100℃保温反应约5h,HPLC检测原料<5%,降温至T<40℃,加入自来水搅拌,过滤;
步骤2、滤饼用5L×3自来水洗涤,60℃鼓风干燥,得645g粗品;滤液静置分层,水层用2L×2甲苯萃取,合并有机相,用3L水洗涤,60℃减压浓缩至干,得粗品250g;
步骤3、645g+250g粗品溶于6L甲醇,加入75g活性炭,室温搅拌,过滤,用1L热甲醇洗涤滤渣,合并滤液,减压浓缩至干,再60℃鼓风干燥,得720g产品。
3.根据权利要求2所述的一种2-氨基-5-碘吡啶的制备方法,其特征在于,所述步骤1中加入20L自来水搅拌0.5h。
4.根据权利要求2所述的一种2-氨基-5-碘吡啶的制备方法,其特征在于,所述步骤3中室温搅拌1h。
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