CN103664759A - 一种3-羟基-2-硝基吡啶的制备方法 - Google Patents
一种3-羟基-2-硝基吡啶的制备方法 Download PDFInfo
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- CN103664759A CN103664759A CN201310646370.8A CN201310646370A CN103664759A CN 103664759 A CN103664759 A CN 103664759A CN 201310646370 A CN201310646370 A CN 201310646370A CN 103664759 A CN103664759 A CN 103664759A
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- Prior art keywords
- nitropyridine
- preparation
- hydroxyl
- hydroxy
- stirring
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- QBPDSKPWYWIHGA-UHFFFAOYSA-N 3-hydroxy-2-nitropyridine Chemical compound OC1=CC=CN=C1[N+]([O-])=O QBPDSKPWYWIHGA-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 238000003756 stirring Methods 0.000 claims abstract description 18
- 239000000203 mixture Substances 0.000 claims abstract description 12
- GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 claims abstract description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000001035 drying Methods 0.000 claims abstract description 6
- 238000001914 filtration Methods 0.000 claims abstract description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 abstract description 7
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 239000002244 precipitate Substances 0.000 abstract 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- 235000011114 ammonium hydroxide Nutrition 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 abstract 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000000644 6-membered heterocyclic compounds Chemical class 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 231100000652 hormesis Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000019633 pungent taste Nutrition 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Abstract
本发明公开了一种3-羟基-2-硝基吡啶的制备方法，包括步骤为：往3-羟基吡啶中边搅拌边加入浓硫酸，并减压条件下使氯化氢挥发，再加入发烟硫酸和发烟硝酸，升温搅拌3-5小时，得到混合物；往所述混合物中滴加浓氨水，调节pH值使pH值为5-5.5，再加入水搅拌得到沉淀物，对沉淀物过滤烘干得到3-羟基-2-硝基吡啶。通过上述方式，本发明的3-羟基-2-硝基吡啶的制备方法，该方法制备过程时间短，既节约了反应过程中的能量损耗，又减少了合成过程中危险的发生，极大的减少了生产成本，得到的3-羟基-2-硝基吡啶纯度高，可以直接进行下一步应用。
Description
技术领域
本发明涉及精细有机合成领域，特别是涉及一种3-羟基-2-硝基吡啶的制备方法。
背景技术
吡啶是一种含有一个氮原子的六元杂环化合物，即苯分子的一个碳被氮取代，它具有许多特殊的药效和结构特性。吡啶衍生物广泛存在于自然界，其中许多物质具有特殊的药理作用。目前吡啶类化合物主要靠化学合成而来。3-羟基-2-硝基吡啶的分子量为C5H4N2O3，分子量为140.09，熔点为67-72℃，是一种刺激性物品，对眼睛、呼吸系统和皮肤均有刺激作用。传统3-羟基-2-硝基吡啶的合成过程中反应时间长，有时甚至一天的时间，容易发生危险。
发明内容
本发明主要解决的技术问题是提供一种3-羟基-2-硝基吡啶的制备方法，该方法操作简单且安全可靠。
为解决上述技术问题，本发明采用的一个技术方案是：提供一种3-羟基-2-硝基吡啶的制备方法，包括步骤为：
（1）往3-羟基吡啶中边搅拌边加入浓硫酸，并减压条件下使氯化氢挥发，再加入发烟硫酸和发烟硝酸，升温搅拌3-5小时，得到混合物；
（2）往所述混合物中滴加浓氨水，调节pH值使pH值为5-5.5，再加入水搅拌得到沉淀物，对沉淀物过滤烘干得到3-羟基-2-硝基吡啶。
在本发明一个较佳实施例中，步骤（1）中所述发烟硫酸的质量百分比为40-50%。
在本发明一个较佳实施例中，步骤（1）中所述升温过程为升温到80-90℃。
在本发明一个较佳实施例中，步骤（2）中所述pH值为5.3。
本发明的有益效果是：本发明的3-羟基-2-硝基吡啶的制备方法，该方法制备过程时间短，既节约了反应过程中的能量损耗，又减少了合成过程中危险的发生，极大的减少了生产成本，得到的3-羟基-2-硝基吡啶纯度高，可以直接进行下一步应用。
具体实施方式
下面将对本发明实施例中的技术方案进行清楚、完整地描述，显然，所描述的实施例仅是本发明的一部分实施例，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它实施例，都属于本发明保护的范围。
实施例一：
提供一种3-羟基-2-硝基吡啶的制备方法，包括步骤为：
（1）往3-羟基吡啶中边搅拌边加入浓硫酸，并减压条件下使氯化氢挥发，再加入质量百分比为42%的发烟硫酸和发烟硝酸，升温到80℃并搅拌3小时，得到混合物；
（2）往所述混合物中滴加浓氨水，调节pH值使pH值为5.5，再加入水搅拌得到沉淀物，对沉淀物过滤烘干得到3-羟基-2-硝基吡啶。
实施例二：
提供一种3-羟基-2-硝基吡啶的制备方法，包括步骤为：
（1）往3-羟基吡啶中边搅拌边加入浓硫酸，并减压条件下使氯化氢挥发，再加入质量百分比为45%的发烟硫酸和发烟硝酸，升温到84℃并搅拌4.5小时，得到混合物；
（2）往所述混合物中滴加浓氨水，调节pH值使pH值为5.3，再加入水搅拌得到沉淀物，对沉淀物过滤烘干得到3-羟基-2-硝基吡啶。
实施例三：
提供一种3-羟基-2-硝基吡啶的制备方法，包括步骤为：
（1）往3-羟基吡啶中边搅拌边加入浓硫酸，并减压条件下使氯化氢挥发，再加入质量百分比为48%的发烟硫酸和发烟硝酸，升温到87℃并搅拌3.5小时，得到混合物；
（2）往所述混合物中滴加浓氨水，调节pH值使pH值为5，再加入水搅拌得到沉淀物，对沉淀物过滤烘干得到3-羟基-2-硝基吡啶。
以上所述仅为本发明的实施例，并非因此限制本发明的专利范围，凡是利用本发明说明书内容所作的等效结构或等效流程变换，或直接或间接运用在其它相关的技术领域，均同理包括在本发明的专利保护范围内。
Claims (4)
1.一种3-羟基-2-硝基吡啶的制备方法，其特征在于，包括步骤为：
（1）往3-羟基吡啶中边搅拌边加入浓硫酸，并减压条件下使氯化氢挥发，再加入发烟硫酸和发烟硝酸，升温搅拌3-5小时，得到混合物；
（2）往所述混合物中滴加浓氨水，调节pH值使pH值为5-5.5，再加入水搅拌得到沉淀物，对沉淀物过滤烘干得到3-羟基-2-硝基吡啶。
2.根据权利要求1所述的3-羟基-2-硝基吡啶的制备方法，其特征在于，步骤（1）中所述发烟硫酸的质量百分比为40-50%。
3.根据权利要求1所述的3-羟基-2-硝基吡啶的制备方法，其特征在于，步骤（1）中所述升温过程为升温到80-90℃。
4.根据权利要求1所述的3-羟基-2-硝基吡啶的制备方法，其特征在于，步骤（2）中所述pH值为5.3。
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103992267A (zh) * | 2014-06-13 | 2014-08-20 | 梁成 | 一种3-羟基-2-硝基吡啶的制备方法 |
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| WO2010072722A1 (en) * | 2008-12-23 | 2010-07-01 | Glaxo Group Limited | Piperidine derivatives useful as orexin antagonists |
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2013
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| CN103992267A (zh) * | 2014-06-13 | 2014-08-20 | 梁成 | 一种3-羟基-2-硝基吡啶的制备方法 |
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Application publication date: 20140326 |