IL47057A - Process for the preparation of 2 - amino-5 - chloropyridine - Google Patents
Process for the preparation of 2 - amino-5 - chloropyridineInfo
- Publication number
- IL47057A IL47057A IL47057A IL4705775A IL47057A IL 47057 A IL47057 A IL 47057A IL 47057 A IL47057 A IL 47057A IL 4705775 A IL4705775 A IL 4705775A IL 47057 A IL47057 A IL 47057A
- Authority
- IL
- Israel
- Prior art keywords
- amino
- chloropyridine
- percent
- chlorinating agent
- medium
- Prior art date
Links
- MAXBVGJEFDMHNV-UHFFFAOYSA-N 5-chloropyridin-2-amine Chemical compound NC1=CC=C(Cl)C=N1 MAXBVGJEFDMHNV-UHFFFAOYSA-N 0.000 title claims description 25
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 32
- 239000012320 chlorinating reagent Substances 0.000 claims description 25
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 24
- 230000002378 acidificating effect Effects 0.000 claims description 23
- 238000005660 chlorination reaction Methods 0.000 claims description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 17
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group 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
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 description 23
- 239000000243 solution Substances 0.000 description 15
- 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 12
- 239000000460 chlorine Substances 0.000 description 12
- 229910052801 chlorine Inorganic materials 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 7
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-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
- 239000002798 polar solvent Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 230000005588 protonation Effects 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- 229960004424 carbon dioxide Drugs 0.000 description 3
- 235000011089 carbon dioxide Nutrition 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000010992 reflux Methods 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 chloro-substituted-imidazo-pyridine Chemical class 0.000 description 2
- 230000002860 competitive effect Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 125000003963 dichloro group Chemical group Cl* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 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
- 238000003756 stirring Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 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
- 150000007513 acids Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 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
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 230000001627 detrimental effect Effects 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
- 150000002431 hydrogen Chemical class 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 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
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000001139 pH measurement Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000013022 venting Methods 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 (2)
| Publication Number | Publication Date |
|---|---|
| IL47057A0 IL47057A0 (en) | 1975-06-25 |
| IL47057A true IL47057A (en) | 1977-08-31 |
Family
ID=23895162
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL47057A IL47057A (en) | 1974-06-07 | 1975-04-09 | Process for the preparation of 2 - amino-5 - chloropyridine |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3985759A (cs) |
| JP (1) | JPS516968A (cs) |
| BE (1) | BE829888A (cs) |
| BR (1) | BR7503403A (cs) |
| CA (1) | CA1032542A (cs) |
| CH (1) | CH598223A5 (cs) |
| DE (1) | DE2520726A1 (cs) |
| FR (1) | FR2273805A1 (cs) |
| GB (1) | GB1505393A (cs) |
| IE (1) | IE41230B1 (cs) |
| IL (1) | IL47057A (cs) |
| IT (1) | IT1038749B (cs) |
| NL (1) | NL7506122A (cs) |
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 (cs) * | 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 IL IL47057A patent/IL47057A/en unknown
- 1975-04-09 IE IE801/75A patent/IE41230B1/xx 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 |
|---|---|
| CH598223A5 (cs) | 1978-04-28 |
| FR2273805B1 (cs) | 1979-08-10 |
| CA1032542A (en) | 1978-06-06 |
| IT1038749B (it) | 1979-11-30 |
| FR2273805A1 (fr) | 1976-01-02 |
| IE41230L (en) | 1975-12-07 |
| US3985759A (en) | 1976-10-12 |
| IE41230B1 (en) | 1979-11-21 |
| BR7503403A (pt) | 1976-06-22 |
| NL7506122A (nl) | 1975-12-09 |
| BE829888A (fr) | 1975-12-05 |
| USB477252I5 (cs) | 1976-01-13 |
| GB1505393A (en) | 1978-03-30 |
| IL47057A0 (en) | 1975-06-25 |
| JPS516968A (en) | 1976-01-20 |
| DE2520726A1 (de) | 1975-12-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| WO2003062143A1 (en) | Preparation of non-hazardous brominating reagents | |
| KR930005446B1 (ko) | 2-알콕시-n-(1-아자비사이클로[2.2.2]옥탄-3-일)아미노 벤즈아미드의 제조방법 | |
| US6740253B2 (en) | Preparation of non-hazardous brominating reagents | |
| US20020103378A1 (en) | Method for carbamoylating alcohols | |
| JPH0532610A (ja) | １，２−ナフトキノンジアジド−５−スルホニルクロリドの製造方法 | |
| US3985759A (en) | Process for preparing 2-amino-5-chloropyridine | |
| KR20070039948A (ko) | 2-아미노-5-요오도 안식향산의 제조 방법 | |
| US4169952A (en) | Process for the preparation of cyclohexanone-2-carboxamide | |
| US4517129A (en) | Process for the preparation of cyanotetrachlorobenzenes | |
| US4996377A (en) | Preparation of aliphatically substituted fluorobenzenes | |
| Markish et al. | New Aspects on the Preparation of 1, 3-Dibromo-5, 5-dimethylhydantoin | |
| EP0307481A1 (en) | Process for preparing 3-chloro-4-fluoronitrobenzene | |
| JP2662508B2 (ja) | ４−メチルスルホニル−１−メチル−２−クロルベンゼンの製法 | |
| JP3704166B2 (ja) | ４−アルキル−３−クロロアルキルスルホニルベンゼンの製造方法 | |
| US3965172A (en) | Production of N,N-dichloro-terephthalamide and N,N-dichloro-isophthalamide | |
| US3947512A (en) | Process for the manufacture of aromatic sulfonic acid halides | |
| US3349111A (en) | Process for the preparation of 3, 5-dibromo-4-hydroxybenzonitrile | |
| JPH09169673A (ja) | ３，５−ビス（トリフルオロメチル）ブロムベンゼンの製造法 | |
| EP0274194A1 (en) | Process for the preparation of 2-nitro-5-phenoxy-N-alkylsulfonyl benzamides by nitration | |
| US5196593A (en) | Halogenated trifluoromethylbenzenes | |
| JPH02169561A (ja) | ３‐トリフルオロメチルベンゼンスルホニルクロリド類の製造方法 | |
| SU1249014A1 (ru) | Способ получени мета-аминобензойной кислоты | |
| KR20010005843A (ko) | 2,6-디클로로-5-플루오로니코티노니트릴의 제조 방법 및 화합물 3-시아노-2-히드록시-5-플루오로피리드-6-온- 일나트륨염과 그의 토토머 | |
| JP3927835B2 (ja) | ヨウ化芳香族化合物ジアセテートの製造方法 | |
| JP3965787B2 (ja) | ２−クロロ−５−ヒドロキシピリジンの製造方法 |