DE2143989C3 - Verfahren zur Herstellung von 2-Methyl-pyridin-3-ol-Derivaten - Google Patents
Verfahren zur Herstellung von 2-Methyl-pyridin-3-ol-DerivatenInfo
- Publication number
- DE2143989C3 DE2143989C3 DE2143989A DE2143989A DE2143989C3 DE 2143989 C3 DE2143989 C3 DE 2143989C3 DE 2143989 A DE2143989 A DE 2143989A DE 2143989 A DE2143989 A DE 2143989A DE 2143989 C3 DE2143989 C3 DE 2143989C3
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- pyridin
- reaction
- derivatives
- methyloxazole
- 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 18
- 230000008569 process Effects 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 6
- AQSRRZGQRFFFGS-UHFFFAOYSA-N 2-methylpyridin-3-ol Chemical class CC1=NC=CC=C1O AQSRRZGQRFFFGS-UHFFFAOYSA-N 0.000 title description 3
- 238000006243 chemical reaction Methods 0.000 description 20
- PUMREIFKTMLCAF-UHFFFAOYSA-N 4-methyl-1,3-oxazole Chemical compound CC1=COC=N1 PUMREIFKTMLCAF-UHFFFAOYSA-N 0.000 description 18
- -1 cycloalkyl radical Chemical class 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 150000003254 radicals Chemical class 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- SVLTYIBILQBQNY-UHFFFAOYSA-N 3-methylsulfonyl-2,5-dihydrofuran Chemical compound CS(=O)(=O)C1=CCOC1 SVLTYIBILQBQNY-UHFFFAOYSA-N 0.000 description 6
- QRDCHUFJZIEHIY-UHFFFAOYSA-N 5-methoxy-2,4-dimethyl-7-oxa-3-azabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound N1=C(C)C(OC)=C2OC2=C1C QRDCHUFJZIEHIY-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 150000003227 pyridoxines Chemical class 0.000 description 6
- 150000003457 sulfones Chemical class 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 235000008160 pyridoxine Nutrition 0.000 description 5
- 239000011677 pyridoxine Substances 0.000 description 5
- 229940011671 vitamin b6 Drugs 0.000 description 5
- ARGCQEVBJHPOGB-UHFFFAOYSA-N 2,5-dihydrofuran Chemical compound C1OCC=C1 ARGCQEVBJHPOGB-UHFFFAOYSA-N 0.000 description 4
- XEKDTIOTHZWKGM-UHFFFAOYSA-N 3-(benzenesulfonyl)-2,5-dihydrofuran Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CCOC1 XEKDTIOTHZWKGM-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 230000009102 absorption Effects 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- RFEIULCTYDOAOA-UHFFFAOYSA-N 5-methylsulfonyl-4,7-dihydro-1,3-dioxepine Chemical compound CS(=O)(=O)C1=CCOCOC1 RFEIULCTYDOAOA-UHFFFAOYSA-N 0.000 description 3
- OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 3
- 125000000068 chlorophenyl group Chemical group 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 239000012433 hydrogen halide Substances 0.000 description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- PPTFGFBOMNJZRD-UHFFFAOYSA-N 4,5-bis(methoxymethyl)-2-methylpyridin-3-ol Chemical compound COCC1=CN=C(C)C(O)=C1COC PPTFGFBOMNJZRD-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- BVFGUTOBJGRJDL-UHFFFAOYSA-N Cl.CC1=NC(=C2C(=C1OC)O2)C Chemical compound Cl.CC1=NC(=C2C(=C1OC)O2)C BVFGUTOBJGRJDL-UHFFFAOYSA-N 0.000 description 2
- 238000005698 Diels-Alder reaction Methods 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WIRUZQNBHNAMAB-UHFFFAOYSA-N benzene;cyclohexane Chemical compound C1CCCCC1.C1=CC=CC=C1 WIRUZQNBHNAMAB-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- LSOBPYSQSPIQJF-UHFFFAOYSA-N but-2-yne Chemical class [CH2]C#CC LSOBPYSQSPIQJF-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical class C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RXNMLQHZBCJMBA-ONEGZZNKSA-N (e)-1,4-dimethoxybut-2-ene Chemical compound COC\C=C\COC RXNMLQHZBCJMBA-ONEGZZNKSA-N 0.000 description 1
- ORTVZLZNOYNASJ-UPHRSURJSA-N (z)-but-2-ene-1,4-diol Chemical class OC\C=C/CO ORTVZLZNOYNASJ-UPHRSURJSA-N 0.000 description 1
- OXNZXQAQUISUME-UHFFFAOYSA-N 1,4-dimethoxy-2-methylsulfonylbut-2-ene Chemical compound COCC=C(S(C)(=O)=O)COC OXNZXQAQUISUME-UHFFFAOYSA-N 0.000 description 1
- HMCUNLUHTBHKTB-UHFFFAOYSA-N 1,4-dimethoxybutane Chemical compound COCCCCOC HMCUNLUHTBHKTB-UHFFFAOYSA-N 0.000 description 1
- DQGMASZUGMDEFA-UHFFFAOYSA-N 1-methyl-2-nitrosoimidazole Chemical compound CN1C=CN=C1N=O DQGMASZUGMDEFA-UHFFFAOYSA-N 0.000 description 1
- YVFYBLLLHYPQOH-UHFFFAOYSA-N 2-(methoxymethyl)pyridin-3-ol Chemical compound COCC1=NC=CC=C1O YVFYBLLLHYPQOH-UHFFFAOYSA-N 0.000 description 1
- OMVGDFRDNLGVQT-UHFFFAOYSA-N 2-chloro-1,4-dimethoxy-3-methylsulfonylbutane Chemical compound CS(=O)(=O)C(COC)C(COC)Cl OMVGDFRDNLGVQT-UHFFFAOYSA-N 0.000 description 1
- JOWXBGIZDALBJW-UHFFFAOYSA-N 3h-dioxepine Chemical group C1OOC=CC=C1 JOWXBGIZDALBJW-UHFFFAOYSA-N 0.000 description 1
- PKVDJMWOJOFJGX-UHFFFAOYSA-N 4,5-bis(methoxymethyl)-2-methylpyridin-3-ol;hydrochloride Chemical compound Cl.COCC1=CN=C(C)C(O)=C1COC PKVDJMWOJOFJGX-UHFFFAOYSA-N 0.000 description 1
- BAKUAUDFCNFLBX-UHFFFAOYSA-N 4,7-dihydro-1,3-dioxepine Chemical compound C1OCC=CCO1 BAKUAUDFCNFLBX-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- AANQLDBTPDQWBO-UHFFFAOYSA-N C(C1=CC=CC=C1)S(=O)(=O)C(COC(C)=O)=CCOC(C)=O Chemical compound C(C1=CC=CC=C1)S(=O)(=O)C(COC(C)=O)=CCOC(C)=O AANQLDBTPDQWBO-UHFFFAOYSA-N 0.000 description 1
- IOTGFHWARJJIHN-UHFFFAOYSA-N C1(=CC=CC=C1)S(=O)(=O)C(COC)=CCOC Chemical compound C1(=CC=CC=C1)S(=O)(=O)C(COC)=CCOC IOTGFHWARJJIHN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- ZMGSBXQRZZGAEQ-UHFFFAOYSA-N FC(S(=O)(=O)C(COC)=CCOC)(F)F Chemical compound FC(S(=O)(=O)C(COC)=CCOC)(F)F ZMGSBXQRZZGAEQ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical class C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- DDCYYCUMAFYDDU-UHFFFAOYSA-N methyl thiohypochlorite Chemical compound CSCl DDCYYCUMAFYDDU-UHFFFAOYSA-N 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- JWUKZUIGOJBEPC-UHFFFAOYSA-N phenyl thiohypochlorite Chemical compound ClSC1=CC=CC=C1 JWUKZUIGOJBEPC-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003455 sulfinic acids Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- 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
- C07D213/66—One oxygen atom attached in position 3 or 5 having in position 3 an oxygen atom and in each of the positions 4 and 5 a carbon atom bound to an oxygen, sulphur, or nitrogen atom, e.g. pyridoxal
- C07D213/67—2-Methyl-3-hydroxy-4,5-bis(hydroxy-methyl)pyridine, i.e. pyridoxine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2143989A DE2143989C3 (de) | 1971-09-02 | 1971-09-02 | Verfahren zur Herstellung von 2-Methyl-pyridin-3-ol-Derivaten |
| US283170A US3876649A (en) | 1971-09-02 | 1972-08-23 | Production of 2-methylpyridin-3-ol derivatives |
| CA150,309A CA996118A (en) | 1971-09-02 | 1972-08-24 | Production of pyridoxine derivatives |
| FR7230783A FR2150980B1 (enExample) | 1971-09-02 | 1972-08-30 | |
| CH1288072A CH587825A5 (enExample) | 1971-09-02 | 1972-08-31 | |
| JP47086777A JPS5744670B2 (enExample) | 1971-09-02 | 1972-08-31 | |
| GB4063572A GB1392558A (en) | 1971-09-02 | 1972-09-01 | Production of 2-methylpyridin-3-ol derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2143989A DE2143989C3 (de) | 1971-09-02 | 1971-09-02 | Verfahren zur Herstellung von 2-Methyl-pyridin-3-ol-Derivaten |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2143989A1 DE2143989A1 (de) | 1973-03-15 |
| DE2143989B2 DE2143989B2 (de) | 1979-04-19 |
| DE2143989C3 true DE2143989C3 (de) | 1979-12-06 |
Family
ID=5818484
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2143989A Expired DE2143989C3 (de) | 1971-09-02 | 1971-09-02 | Verfahren zur Herstellung von 2-Methyl-pyridin-3-ol-Derivaten |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3876649A (enExample) |
| JP (1) | JPS5744670B2 (enExample) |
| CA (1) | CA996118A (enExample) |
| CH (1) | CH587825A5 (enExample) |
| DE (1) | DE2143989C3 (enExample) |
| FR (1) | FR2150980B1 (enExample) |
| GB (1) | GB1392558A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2451725A1 (de) * | 1974-10-31 | 1976-05-13 | Basf Ag | Verfahren zur herstellung von 4methyloxazol |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4402236C2 (de) * | 1994-01-26 | 1996-09-26 | Braun Ag | Verfahren zum Betrieb einer Reinigungsvorrichtung für den Scherkopf eines Trockenrasierapparates |
| DE4402238C2 (de) * | 1994-01-26 | 1996-09-26 | Braun Ag | Reinigungsvorrichtung für den Scherkopf eines Trockenrasierers |
| DE4402237C1 (de) * | 1994-01-26 | 1995-03-09 | Braun Ag | Reinigungsvorrichtung zur Reinigung des Scherkopfs eines Trockenrasierapparats |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3227724A (en) * | 1962-01-16 | 1966-01-04 | Merck & Co Inc | Process for preparing 2-methyl-3-hydroxypyridines |
| US3381014A (en) * | 1965-12-30 | 1968-04-30 | Merck & Co Inc | Process for producing pyridoxine and novel intermediates thereof |
| US3525749A (en) * | 1969-03-19 | 1970-08-25 | Merck & Co Inc | Certain 1,3-dioxepino-(5,6-c)-pyridines |
-
1971
- 1971-09-02 DE DE2143989A patent/DE2143989C3/de not_active Expired
-
1972
- 1972-08-23 US US283170A patent/US3876649A/en not_active Expired - Lifetime
- 1972-08-24 CA CA150,309A patent/CA996118A/en not_active Expired
- 1972-08-30 FR FR7230783A patent/FR2150980B1/fr not_active Expired
- 1972-08-31 JP JP47086777A patent/JPS5744670B2/ja not_active Expired
- 1972-08-31 CH CH1288072A patent/CH587825A5/xx not_active IP Right Cessation
- 1972-09-01 GB GB4063572A patent/GB1392558A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2451725A1 (de) * | 1974-10-31 | 1976-05-13 | Basf Ag | Verfahren zur herstellung von 4methyloxazol |
| DE2451725C2 (de) * | 1974-10-31 | 1983-05-19 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von 4- Methyloxazol |
Also Published As
| Publication number | Publication date |
|---|---|
| CH587825A5 (enExample) | 1977-05-13 |
| CA996118A (en) | 1976-08-31 |
| FR2150980B1 (enExample) | 1977-12-23 |
| GB1392558A (en) | 1975-04-30 |
| US3876649A (en) | 1975-04-08 |
| JPS4834177A (enExample) | 1973-05-16 |
| DE2143989B2 (de) | 1979-04-19 |
| DE2143989A1 (de) | 1973-03-15 |
| FR2150980A1 (enExample) | 1973-04-13 |
| JPS5744670B2 (enExample) | 1982-09-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8330 | Complete disclaimer |