SK71698A3 - Process for the preparation of methoxyiminophenylglyoxylic acid derivatives - Google Patents

Process for the preparation of methoxyiminophenylglyoxylic acid derivatives Download PDF

Info

Publication number: SK71698A3
Authority: SK; Slovakia
Prior art keywords: formula; carbon atoms; acid; alkyl; iii
Prior art date: 1995-11-29

Application number

SK716-98A

Other languages

English (en)

Slovak (sk)

Inventor

Jean-Marie Assercq

Richard Breitschuh

Werner Pfaff

Original Assignee

Novartis Ag

Priority date (The priority date 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 date listed.)

1995-11-29

Filing date

1996-11-18

Publication date

1998-11-04

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=25684617&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=SK71698(A3) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1996-11-18 Application filed by Novartis Ag filed Critical Novartis Ag

1998-11-04 Publication of SK71698A3 publication Critical patent/SK71698A3/sk

Links

238000000034 method Methods 0.000 title claims abstract description 27
238000002360 preparation method Methods 0.000 title claims abstract description 18
MLKSCLQIGHXRQF-UHFFFAOYSA-N 2-(6-methoxyiminocyclohexa-2,4-dien-1-yl)-2-oxoacetic acid Chemical class CON=C1C=CC=CC1C(=O)C(O)=O MLKSCLQIGHXRQF-UHFFFAOYSA-N 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 26
QSQXKGDDWIFOTQ-UHFFFAOYSA-N 2-[2-(chloromethyl)phenyl]-2-oxoacetamide Chemical compound NC(=O)C(=O)C1=CC=CC=C1CCl QSQXKGDDWIFOTQ-UHFFFAOYSA-N 0.000 claims abstract description 14
150000002148 esters Chemical class 0.000 claims abstract description 12
GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 claims abstract description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 17
125000004432 carbon atom Chemical group C* 0.000 claims description 17
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 16
238000006243 chemical reaction Methods 0.000 claims description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
125000003118 aryl group Chemical group 0.000 claims description 8
239000003085 diluting agent Substances 0.000 claims description 6
MVJIUTPZBDDMPF-UHFFFAOYSA-N 2-(chloromethyl)benzoyl cyanide Chemical compound ClCC1=CC=CC=C1C(=O)C#N MVJIUTPZBDDMPF-UHFFFAOYSA-N 0.000 claims description 5
230000032050 esterification Effects 0.000 claims description 5
238000005886 esterification reaction Methods 0.000 claims description 5
230000002378 acidificating effect Effects 0.000 claims description 4
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
125000001188 haloalkyl group Chemical group 0.000 claims 3
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
238000005903 acid hydrolysis reaction Methods 0.000 claims 1
125000003710 aryl alkyl group Chemical group 0.000 claims 1
238000006146 oximation reaction Methods 0.000 claims 1
239000000376 reactant Substances 0.000 claims 1
239000002253 acid Substances 0.000 abstract description 19
239000000417 fungicide Substances 0.000 abstract description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
239000000543 intermediate Substances 0.000 description 7
239000000203 mixture Substances 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
229910000041 hydrogen chloride Inorganic materials 0.000 description 6
239000000047 product Substances 0.000 description 6
239000007789 gas Substances 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
-1 haloalkyl carbon Chemical class 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
150000004702 methyl esters Chemical class 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000012452 mother liquor Substances 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 2
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000011707 mineral Substances 0.000 description 2
TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000000575 pesticide Substances 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
238000007127 saponification reaction Methods 0.000 description 2
239000000243 solution Substances 0.000 description 2
150000003460 sulfonic acids Chemical class 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
239000008096 xylene Substances 0.000 description 2
QQGVWMIRCZEUBB-AWNIVKPZSA-N (ne)-n-[1-[3-(trifluoromethyl)phenyl]ethylidene]hydroxylamine Chemical compound O\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 QQGVWMIRCZEUBB-AWNIVKPZSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
HWTDMFJYBAURQR-UHFFFAOYSA-N 80-82-0 Chemical compound OS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O HWTDMFJYBAURQR-UHFFFAOYSA-N 0.000 description 1
125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
FXZNPTMZAZZPHT-UHFFFAOYSA-N CON=CC(=O)OCCCCC Chemical compound CON=CC(=O)OCCCCC FXZNPTMZAZZPHT-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
230000000895 acaricidal effect Effects 0.000 description 1
239000000642 acaricide Substances 0.000 description 1
ZIXLDMFVRPABBX-UHFFFAOYSA-N alpha-methylcyclopentanone Natural products CC1CCCC1=O ZIXLDMFVRPABBX-UHFFFAOYSA-N 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
VQAKRCMNKHPGJX-UHFFFAOYSA-N chloromethyl 2-oxo-2-phenylacetate Chemical compound ClCOC(C(=O)C1=CC=CC=C1)=O VQAKRCMNKHPGJX-UHFFFAOYSA-N 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
239000010779 crude oil Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000001914 filtration Methods 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
238000006140 methanolysis reaction Methods 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 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
238000005809 transesterification reaction Methods 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/72—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
- C07C235/76—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
- C07C235/78—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/08—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reaction of hydroxylamines with carbonyl compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
- C07C251/60—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by carboxyl groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SK716-98A 1995-11-29 1996-11-18 Process for the preparation of methoxyiminophenylglyoxylic acid derivatives SK71698A3 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
CH338895		1995-11-29
CH45196		1996-02-21
PCT/EP1996/005057 WO1997019912A1 (en)	1995-11-29	1996-11-18	Process for the preparation of methoxyminophenylglyoxylic acid derivatives

Publications (1)

Publication Number	Publication Date
SK71698A3 true SK71698A3 (en)	1998-11-04

Family

ID=25684617

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK716-98A SK71698A3 (en)	1995-11-29	1996-11-18	Process for the preparation of methoxyiminophenylglyoxylic acid derivatives

Country Status (16)

Country	Link
EP (1)	EP0874807B2 (da)
JP (1)	JP2000500766A (da)
CN (1)	CN1203583A (da)
AT (1)	ATE213493T1 (da)
AU (1)	AU7692796A (da)
BR (1)	BR9611789A (da)
CA (1)	CA2235587A1 (da)
CZ (1)	CZ163098A3 (da)
DE (1)	DE69619402T3 (da)
DK (1)	DK0874807T4 (da)
ES (1)	ES2173330T5 (da)
HU (1)	HUP9903773A2 (da)
MX (1)	MX9804264A (da)
PL (1)	PL326563A1 (da)
SK (1)	SK71698A3 (da)
WO (1)	WO1997019912A1 (da)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE161007T1 (de) *	1990-06-27	1997-12-15	Basf Ag	O-benzyl-oximether und diese verbindungen enthaltende pflanzenschutzmittel
US6211413B1 (en)	1998-01-13	2001-04-03	Bayer Aktiengesellschaft	Process for the preparation of phenyl alkyl ketones and benzaldehydes
CN106431977B (zh) *	2015-08-12	2018-11-02	沈阳中化农药化工研发有限公司	一种不饱和肟醚类化合物及其用途
CN106748858B (zh) *	2017-01-11	2018-09-28	青岛昌泰和生物科技有限公司	一种乙醛酰胺化合物的制备方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
PH11991042549B1 (da) *	1990-06-05	2000-12-04
ATE161007T1 (de) *	1990-06-27	1997-12-15	Basf Ag	O-benzyl-oximether und diese verbindungen enthaltende pflanzenschutzmittel
GB9018408D0 (en) *	1990-08-22	1990-10-03	Ici Plc	Fungicides
JP3121061B2 (ja) *	1991-10-04	2000-12-25	塩野義製薬株式会社	アルコキシイミノアセトアミド類製造用中間体の製造法およびそれに用いる中間体
AU686821B2 (en) *	1994-06-10	1998-02-12	Basf Aktiengesellschaft	Method of preparing alpha-methoxyiminocarboxylic acid methylamides, and intermediates used in the method

1996
- 1996-11-18 CN CN96198702A patent/CN1203583A/zh active Pending
- 1996-11-18 DE DE69619402T patent/DE69619402T3/de not_active Expired - Lifetime
- 1996-11-18 SK SK716-98A patent/SK71698A3/sk unknown
- 1996-11-18 CZ CZ981630A patent/CZ163098A3/cs unknown
- 1996-11-18 BR BR9611789A patent/BR9611789A/pt not_active Application Discontinuation
- 1996-11-18 AU AU76927/96A patent/AU7692796A/en not_active Abandoned
- 1996-11-18 JP JP9520128A patent/JP2000500766A/ja active Pending
- 1996-11-18 WO PCT/EP1996/005057 patent/WO1997019912A1/en not_active Ceased
- 1996-11-18 DK DK96939832T patent/DK0874807T4/da active
- 1996-11-18 EP EP96939832A patent/EP0874807B2/en not_active Expired - Lifetime
- 1996-11-18 ES ES96939832T patent/ES2173330T5/es not_active Expired - Lifetime
- 1996-11-18 PL PL96326563A patent/PL326563A1/xx unknown
- 1996-11-18 AT AT96939832T patent/ATE213493T1/de active
- 1996-11-18 HU HU9903773A patent/HUP9903773A2/hu unknown
- 1996-11-18 CA CA002235587A patent/CA2235587A1/en not_active Abandoned
1998
- 1998-05-28 MX MX9804264A patent/MX9804264A/es unknown

Also Published As

Publication number	Publication date
DE69619402T3 (de)	2007-02-08
EP0874807A1 (en)	1998-11-04
DK0874807T4 (da)	2006-11-20
AU7692796A (en)	1997-06-19
ES2173330T3 (es)	2002-10-16
CN1203583A (zh)	1998-12-30
EP0874807B1 (en)	2002-02-20
HUP9903773A2 (hu)	2000-03-28
DE69619402D1 (de)	2002-03-28
CA2235587A1 (en)	1997-06-05
EP0874807B2 (en)	2006-08-02
BR9611789A (pt)	1999-07-13
DK0874807T3 (da)	2002-05-13
PL326563A1 (en)	1998-09-28
ATE213493T1 (de)	2002-03-15
DE69619402T2 (de)	2003-04-03
ES2173330T5 (es)	2007-03-16
CZ163098A3 (cs)	1998-08-12
WO1997019912A1 (en)	1997-06-05
JP2000500766A (ja)	2000-01-25
MX9804264A (es)	1998-09-30

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