DE2520726A1 - Verfahren zur herstellung von 2-amino-5-chlorpyridin - Google Patents
Verfahren zur herstellung von 2-amino-5-chlorpyridinInfo
- Publication number
- DE2520726A1 DE2520726A1 DE19752520726 DE2520726A DE2520726A1 DE 2520726 A1 DE2520726 A1 DE 2520726A1 DE 19752520726 DE19752520726 DE 19752520726 DE 2520726 A DE2520726 A DE 2520726A DE 2520726 A1 DE2520726 A1 DE 2520726A1
- Authority
- DE
- Germany
- Prior art keywords
- amino
- medium
- chloropyridine
- acid
- reaction mixture
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- MAXBVGJEFDMHNV-UHFFFAOYSA-N 5-chloropyridin-2-amine Chemical compound NC1=CC=C(Cl)C=N1 MAXBVGJEFDMHNV-UHFFFAOYSA-N 0.000 title claims description 24
- 238000000034 method Methods 0.000 title claims description 23
- 238000002360 preparation method Methods 0.000 title description 4
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 34
- 230000002378 acidificating effect Effects 0.000 claims description 25
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 24
- 239000012320 chlorinating reagent Substances 0.000 claims description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 21
- 238000005660 chlorination reaction Methods 0.000 claims description 11
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 9
- 229960000583 acetic acid Drugs 0.000 claims description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 6
- 239000012362 glacial acetic acid Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 description 23
- 235000019647 acidic taste Nutrition 0.000 description 19
- 239000000243 solution Substances 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000006227 byproduct Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
- OCWBGKZFOYMCCN-UHFFFAOYSA-N 3,5-dichloropyridin-2-amine Chemical compound NC1=NC=C(Cl)C=C1Cl OCWBGKZFOYMCCN-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 239000002798 polar solvent Substances 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- 235000011089 carbon dioxide Nutrition 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 230000005588 protonation Effects 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 150000003930 2-aminopyridines Chemical class 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- -1 chlorine-substituted imidazopyridines Chemical class 0.000 description 2
- 125000003963 dichloro group Chemical group Cl* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 150000005793 2-amino-5-chloropyridine Chemical class 0.000 description 1
- QLILRKBRWXALIE-UHFFFAOYSA-N 3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1 QLILRKBRWXALIE-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
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 206010000210 abortion Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000001139 pH measurement Methods 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 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
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/477,252 US3985759A (en) | 1974-06-07 | 1974-06-07 | Process for preparing 2-amino-5-chloropyridine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2520726A1 true DE2520726A1 (de) | 1975-12-18 |
Family
ID=23895162
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752520726 Withdrawn DE2520726A1 (de) | 1974-06-07 | 1975-05-09 | Verfahren zur herstellung von 2-amino-5-chlorpyridin |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3985759A (enExample) |
| JP (1) | JPS516968A (enExample) |
| BE (1) | BE829888A (enExample) |
| BR (1) | BR7503403A (enExample) |
| CA (1) | CA1032542A (enExample) |
| CH (1) | CH598223A5 (enExample) |
| DE (1) | DE2520726A1 (enExample) |
| FR (1) | FR2273805A1 (enExample) |
| GB (1) | GB1505393A (enExample) |
| IE (1) | IE41230B1 (enExample) |
| IL (1) | IL47057A (enExample) |
| IT (1) | IT1038749B (enExample) |
| NL (1) | NL7506122A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106432069A (zh) * | 2016-09-09 | 2017-02-22 | 安徽工业大学 | 一种2‑氨基‑5‑氯‑吡啶的制备方法 |
| CN106632014B (zh) * | 2016-12-21 | 2021-06-15 | 嘉兴学院 | 一种2-氨基-5-氯吡啶的制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1232201A (enExample) * | 1967-06-07 | 1971-05-19 | ||
| US3849429A (en) * | 1973-03-30 | 1974-11-19 | Olin Corp | Halogenation of diaminopyridines in acidic media |
-
1974
- 1974-06-07 US US05/477,252 patent/US3985759A/en not_active Expired - Lifetime
-
1975
- 1975-04-07 CA CA223,912A patent/CA1032542A/en not_active Expired
- 1975-04-09 IE IE801/75A patent/IE41230B1/xx unknown
- 1975-04-09 IL IL47057A patent/IL47057A/en unknown
- 1975-05-09 DE DE19752520726 patent/DE2520726A1/de not_active Withdrawn
- 1975-05-23 NL NL7506122A patent/NL7506122A/xx not_active Application Discontinuation
- 1975-05-30 BR BR4359/75D patent/BR7503403A/pt unknown
- 1975-06-03 GB GB23870/75A patent/GB1505393A/en not_active Expired
- 1975-06-05 FR FR7517651A patent/FR2273805A1/fr active Granted
- 1975-06-05 BE BE1006710A patent/BE829888A/xx unknown
- 1975-06-06 IT IT24092/75A patent/IT1038749B/it active
- 1975-06-06 CH CH730975A patent/CH598223A5/xx not_active IP Right Cessation
- 1975-06-07 JP JP50069040A patent/JPS516968A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS516968A (en) | 1976-01-20 |
| IL47057A0 (en) | 1975-06-25 |
| IT1038749B (it) | 1979-11-30 |
| CH598223A5 (enExample) | 1978-04-28 |
| IL47057A (en) | 1977-08-31 |
| IE41230L (en) | 1975-12-07 |
| IE41230B1 (en) | 1979-11-21 |
| GB1505393A (en) | 1978-03-30 |
| FR2273805A1 (fr) | 1976-01-02 |
| NL7506122A (nl) | 1975-12-09 |
| US3985759A (en) | 1976-10-12 |
| BE829888A (fr) | 1975-12-05 |
| CA1032542A (en) | 1978-06-06 |
| BR7503403A (pt) | 1976-06-22 |
| USB477252I5 (enExample) | 1976-01-13 |
| FR2273805B1 (enExample) | 1979-08-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |