DE2460039C3 - Verfahren zur Herstellung von Hydroxymethylpyridinen - Google Patents
Verfahren zur Herstellung von HydroxymethylpyridinenInfo
- Publication number
- DE2460039C3 DE2460039C3 DE19742460039 DE2460039A DE2460039C3 DE 2460039 C3 DE2460039 C3 DE 2460039C3 DE 19742460039 DE19742460039 DE 19742460039 DE 2460039 A DE2460039 A DE 2460039A DE 2460039 C3 DE2460039 C3 DE 2460039C3
- Authority
- DE
- Germany
- Prior art keywords
- pyridines
- pyridine
- hydroxymethyl
- acetoxymethyl
- reaction
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 31
- SHNUBALDGXWUJI-UHFFFAOYSA-N pyridin-2-ylmethanol Chemical class OCC1=CC=CC=N1 SHNUBALDGXWUJI-UHFFFAOYSA-N 0.000 title claims description 23
- 230000008569 process Effects 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 69
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- 239000011541 reaction mixture Substances 0.000 claims description 20
- KEYZUMLVDCHSTP-UHFFFAOYSA-N pyridin-2-ylmethyl acetate Chemical class CC(=O)OCC1=CC=CC=N1 KEYZUMLVDCHSTP-UHFFFAOYSA-N 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 17
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- 239000002585 base Substances 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 13
- XARIFKSEVODEFM-UHFFFAOYSA-N [6-(acetyloxymethyl)pyridin-2-yl]methyl acetate Chemical compound C(C)(=O)OCC1=NC(=CC=C1)COC(C)=O XARIFKSEVODEFM-UHFFFAOYSA-N 0.000 description 12
- 230000007062 hydrolysis Effects 0.000 description 12
- 238000006460 hydrolysis reaction Methods 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 238000006140 methanolysis reaction Methods 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- WWFMINHWJYHXHF-UHFFFAOYSA-N [6-(hydroxymethyl)pyridin-2-yl]methanol Chemical compound OCC1=CC=CC(CO)=N1 WWFMINHWJYHXHF-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 7
- 238000000605 extraction Methods 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- -1 dihydroxymethyl Chemical class 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000000746 purification Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- VSICEQUMRIDAGS-UHFFFAOYSA-N [6-(hydroxymethyl)pyridin-2-yl]methanol;hydrochloride Chemical compound Cl.OCC1=CC=CC(CO)=N1 VSICEQUMRIDAGS-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- DAXJNUBSBFUTRP-RTQNCGMRSA-N (8r,9s,10r,13s,14s)-6-(hydroxymethyl)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthrene-3,17-dione Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC(CO)C2=C1 DAXJNUBSBFUTRP-RTQNCGMRSA-N 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- UAPCKORZDAFJAB-UHFFFAOYSA-N pyridin-2-ylmethanediol Chemical class OC(O)C1=CC=CC=N1 UAPCKORZDAFJAB-UHFFFAOYSA-N 0.000 description 3
- 150000003222 pyridines Chemical class 0.000 description 3
- 238000002798 spectrophotometry method Methods 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- VURSFJLMQCEOCI-UHFFFAOYSA-N (2,6-dimethylpyridin-3-yl) acetate Chemical compound C(C)(=O)OC=1C(=NC(=CC=1)C)C VURSFJLMQCEOCI-UHFFFAOYSA-N 0.000 description 1
- IGUIYPUGCIHEGB-UHFFFAOYSA-N 2-[2-(acetyloxymethyl)pyridin-3-yl]acetic acid Chemical compound CC(=O)OCC1=C(C=CC=N1)CC(=O)O IGUIYPUGCIHEGB-UHFFFAOYSA-N 0.000 description 1
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 1
- UCCJEHMRRPWLHZ-UHFFFAOYSA-N C(C)(=O)OCC1=NC(=CC=C1OC(C)=O)C Chemical compound C(C)(=O)OCC1=NC(=CC=C1OC(C)=O)C UCCJEHMRRPWLHZ-UHFFFAOYSA-N 0.000 description 1
- 235000006481 Colocasia esculenta Nutrition 0.000 description 1
- 240000004270 Colocasia esculenta var. antiquorum Species 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- JGNQWOXGXHTLBL-UHFFFAOYSA-M OCC1=CC=NC=C1.[OH-].[K+] Chemical class OCC1=CC=NC=C1.[OH-].[K+] JGNQWOXGXHTLBL-UHFFFAOYSA-M 0.000 description 1
- 241000863032 Trieres Species 0.000 description 1
- LFQYNSVRPGADOZ-UHFFFAOYSA-N [6-(hydroxymethyl)pyridin-2-yl]methanol;methylcarbamic acid Chemical compound CNC(O)=O.CNC(O)=O.OCC1=CC=CC(CO)=N1 LFQYNSVRPGADOZ-UHFFFAOYSA-N 0.000 description 1
- DBHMEBUYCVXYKO-UHFFFAOYSA-N [acetyloxy(pyridin-2-yl)methyl] acetate Chemical class CC(=O)OC(OC(C)=O)C1=CC=CC=N1 DBHMEBUYCVXYKO-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- PTMBWNZJOQBTBK-UHFFFAOYSA-N pyridin-4-ylmethanol Chemical compound OCC1=CC=NC=C1 PTMBWNZJOQBTBK-UHFFFAOYSA-N 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HURI000533 HU167834B (enrdf_load_stackoverflow) | 1973-12-29 | 1973-12-29 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2460039A1 DE2460039A1 (de) | 1975-07-10 |
| DE2460039B2 DE2460039B2 (de) | 1978-06-29 |
| DE2460039C3 true DE2460039C3 (de) | 1979-03-01 |
Family
ID=11000944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742460039 Expired DE2460039C3 (de) | 1973-12-29 | 1974-12-19 | Verfahren zur Herstellung von Hydroxymethylpyridinen |
Country Status (10)
| Country | Link |
|---|---|
| AT (1) | AT339303B (enrdf_load_stackoverflow) |
| CH (1) | CH601235A5 (enrdf_load_stackoverflow) |
| CS (1) | CS197241B2 (enrdf_load_stackoverflow) |
| DD (1) | DD115903A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2460039C3 (enrdf_load_stackoverflow) |
| ES (1) | ES433392A1 (enrdf_load_stackoverflow) |
| HU (1) | HU167834B (enrdf_load_stackoverflow) |
| PL (1) | PL95853B1 (enrdf_load_stackoverflow) |
| SU (1) | SU510998A3 (enrdf_load_stackoverflow) |
| YU (1) | YU36928B (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2835178A1 (de) * | 1978-08-11 | 1980-02-14 | Adidas Sportschuhe | Sportschuh, insbesondere laufschuh zur verwendung auf harten bahnen |
| DE19542035A1 (de) | 1995-11-10 | 1997-05-15 | Basf Ag | Verfahren zur Herstellung von hydroxyhaltigen Verbindungen aus Ameisensäureestern |
-
1973
- 1973-12-29 HU HURI000533 patent/HU167834B/hu unknown
-
1974
- 1974-12-12 CH CH1654274A patent/CH601235A5/xx not_active IP Right Cessation
- 1974-12-12 AT AT990174A patent/AT339303B/de not_active IP Right Cessation
- 1974-12-19 DE DE19742460039 patent/DE2460039C3/de not_active Expired
- 1974-12-22 CS CS892474A patent/CS197241B2/cs unknown
- 1974-12-23 DD DD18335574A patent/DD115903A5/xx unknown
- 1974-12-26 SU SU2091928A patent/SU510998A3/ru active
- 1974-12-27 YU YU348074A patent/YU36928B/xx unknown
- 1974-12-27 ES ES433392A patent/ES433392A1/es not_active Expired
- 1974-12-28 PL PL17690474A patent/PL95853B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS197241B2 (en) | 1980-04-30 |
| YU348074A (en) | 1982-06-18 |
| HU167834B (enrdf_load_stackoverflow) | 1975-12-25 |
| DE2460039B2 (de) | 1978-06-29 |
| PL95853B1 (pl) | 1977-11-30 |
| SU510998A3 (ru) | 1976-04-15 |
| ES433392A1 (es) | 1976-12-01 |
| DE2460039A1 (de) | 1975-07-10 |
| CH601235A5 (enrdf_load_stackoverflow) | 1978-06-30 |
| YU36928B (en) | 1984-08-31 |
| AT339303B (de) | 1977-10-10 |
| DD115903A5 (enrdf_load_stackoverflow) | 1975-10-20 |
| ATA990174A (de) | 1977-02-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |