CAS： 4548-45-2
MF： C5H3ClN2O2
Appearance： white to light yellow crystal
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Purification Methods |
It crystallises from *benzene or *benzene/pet ether. [Beilstein 20/5 V 452.] |
| Uses | 2-chloro-5-nitropyridine is an important pyridine derivative and is an intermediate for synthesizing bactericides, plant growth regulators, antibiotics and other medicaments. |
| Production Method | A method for preparing 2-chloro-5-nitropyridine, which comprises the following steps of: 1, synthesizing 2-amino-5-nitropyridine; 2, synthesizing 2-hydroxy-5-nitropyridine; and 3, synthesizing the 2-chloro-5-nitropyridine. By the method for preparing the 2-chloro-5-nitropyridine, few byproducts are produced in a digestion process, reaction conditions are mild and total yield is high. |
InChI:InChI=1/C5H3ClN2O2/c6-5-4(8(9)10)2-1-3-7-5/h1-3H
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Based on literature review and mechanism analysis, this paper designed a variety of feasible synthesis methods, compared and evaluated various methods, and determined the best synthesis route: using 2-aminopyridine as the raw material, 2-amino-5-nitropyridine was obtained by mixed acid nitration, and then hydrolyzed under acidic conditions to obtain 2-hydroxy-5-nitropyridine, and finally chlorinated with PCl_5/POCl_3 as a chlorinating agent to obtain 2-chloro-5-nitropyridine, with a total yield of 41.1%; using 2-chloropyridine as the raw material, a one-pot method was used to obtain 2-chloro-4-nitropyridine-N-oxide by N-oxidation and mixed acid nitration, and finally 4-amino-2-chloropyridine was obtained by reduction, with a total yield of 69%.
The chlorination of hydroxy aza-arenes w...
Background and Purpose: Malaria is one o...
3-nitropyridine N-oxide
2-chloro-5-nitropyridine
2-Chloro-3-nitropyridine
| Conditions | Yield |
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With trichlorophosphate; at 110 ℃; for 2h; Yield given. Yields of byproduct given;
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5-nitro-pyridin-2-ylamine
2-chloro-5-nitropyridine
| Conditions | Yield |
|---|---|
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With pyrylium tetrafluoroborate; magnesium chloride; In acetonitrile; for 16h; Heating; Sealed tube;
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86% |
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With hydrogenchloride; sodium nitrite;
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Multi-step reaction with 2 steps
1: 77 percent / aq. H2SO4; NaNO2 / 0 - 20 °C
2: 66 percent / POCl3; PCl5 / 3 h / 110 °C
With phosphorus pentachloride; sulfuric acid; sodium nitrite; trichlorophosphate;
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Multi-step reaction with 2 steps
1: hydrogenchloride; sodium nitrite / water / 0.67 h / 0 - 6 °C
2: trichlorophosphate / N,N-dimethyl-formamide / 2 h / 20 °C / Reflux
With hydrogenchloride; sodium nitrite; trichlorophosphate; In water; N,N-dimethyl-formamide;
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Multi-step reaction with 2 steps
1: sodium hydroxide / Reflux
2: trichlorophosphate / N,N-dimethyl-formamide / Reflux
With sodium hydroxide; trichlorophosphate; In N,N-dimethyl-formamide;
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5-nitro-2-hydroxypyridine
5-nitro-pyridin-2-ylamine
phosgene
1-methyl-5-nitro-2(1H)-pyridone
5-nitro-2-piperidinopyridine
4-(5-nitro-pyridin-2-yl)-morpholine
3-Amino-5'-nitro-2,2'-dipyridyl-sulfid
2-(methyl(5-nitropyridin-2-yl)amino)ethanol
