DE3707530A1 - Neue substituierte dihalogenpyridine und verfahren zu ihrer herstellung sowie ihre weitere umsetzung zu pyridindicarbonsaeurediestern - Google Patents
Neue substituierte dihalogenpyridine und verfahren zu ihrer herstellung sowie ihre weitere umsetzung zu pyridindicarbonsaeurediesternInfo
- Publication number
- DE3707530A1 DE3707530A1 DE19873707530 DE3707530A DE3707530A1 DE 3707530 A1 DE3707530 A1 DE 3707530A1 DE 19873707530 DE19873707530 DE 19873707530 DE 3707530 A DE3707530 A DE 3707530A DE 3707530 A1 DE3707530 A1 DE 3707530A1
- Authority
- DE
- Germany
- Prior art keywords
- compound
- group
- general formula
- compounds
- formula
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 14
- -1 PYRIDINE DICARBONIC ACID DIESTERS Chemical class 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 43
- 238000010992 reflux Methods 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000007857 hydrazones Chemical class 0.000 claims description 5
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229960003512 nicotinic acid Drugs 0.000 claims description 2
- 239000011664 nicotinic acid Substances 0.000 claims description 2
- 235000001968 nicotinic acid Nutrition 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 4
- 230000009615 deamination Effects 0.000 description 4
- 238000006481 deamination reaction Methods 0.000 description 4
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 description 4
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 229910052763 palladium 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
- 239000002244 precipitate Substances 0.000 description 3
- 238000007142 ring opening reaction Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- JPIJMXOJEHMTPU-UHFFFAOYSA-N 5-methylpyridine-2,3-dicarboxylic acid Chemical compound CC1=CN=C(C(O)=O)C(C(O)=O)=C1 JPIJMXOJEHMTPU-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- VHILMKFSCRWWIJ-UHFFFAOYSA-N dimethyl acetylenedicarboxylate Chemical compound COC(=O)C#CC(=O)OC VHILMKFSCRWWIJ-UHFFFAOYSA-N 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 230000008635 plant growth Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- MTAVBTGOXNGCJR-UHFFFAOYSA-N 5-ethylpyridine-2,3-dicarboxylic acid Chemical compound CCC1=CN=C(C(O)=O)C(C(O)=O)=C1 MTAVBTGOXNGCJR-UHFFFAOYSA-N 0.000 description 1
- PVSGXWMWNRGTKE-UHFFFAOYSA-N 5-methyl-2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]pyridine-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=C(C)C=C1C(O)=O PVSGXWMWNRGTKE-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XVOKUMIPKHGGTN-UHFFFAOYSA-N Imazethapyr Chemical compound OC(=O)C1=CC(CC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 XVOKUMIPKHGGTN-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- VPODXHOUBDCEHN-UHFFFAOYSA-N pyridine-3-carbonyl pyridine-3-carboxylate Chemical class C=1C=CN=CC=1C(=O)OC(=O)C1=CC=CN=C1 VPODXHOUBDCEHN-UHFFFAOYSA-N 0.000 description 1
- GJAWHXHKYYXBSV-UHFFFAOYSA-N pyridinedicarboxylic acid Natural products OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/803—Processes of preparation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/98—Nitrogen atom
-
- 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB868605868A GB8605868D0 (en) | 1986-03-10 | 1986-03-10 | Preparation of heterocyclic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3707530A1 true DE3707530A1 (de) | 1987-09-17 |
Family
ID=10594328
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19873707530 Ceased DE3707530A1 (de) | 1986-03-10 | 1987-03-09 | Neue substituierte dihalogenpyridine und verfahren zu ihrer herstellung sowie ihre weitere umsetzung zu pyridindicarbonsaeurediestern |
Country Status (7)
| Country | Link |
|---|---|
| JP (2) | JPH0832683B2 (enrdf_load_stackoverflow) |
| BE (1) | BE1003158A5 (enrdf_load_stackoverflow) |
| CH (1) | CH671762A5 (enrdf_load_stackoverflow) |
| DE (1) | DE3707530A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2595354B1 (enrdf_load_stackoverflow) |
| GB (2) | GB8605868D0 (enrdf_load_stackoverflow) |
| NL (1) | NL8700324A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996037471A1 (de) * | 1995-05-22 | 1996-11-28 | Basf Aktiengesellschaft | N-aminopyridonderivate und ihre verwendung als herbizide |
| CN108495845A (zh) * | 2016-01-22 | 2018-09-04 | 美国陶氏益农公司 | 制备4-烷氧基-3-乙酰氧基吡啶甲酸的方法 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI506019B (zh) * | 2008-12-08 | 2015-11-01 | Basf Se | 製造經取代５－甲氧基甲基吡啶－２，３－二羧酸衍生物之方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0161221A2 (de) * | 1984-05-11 | 1985-11-13 | Ciba-Geigy Ag | Verfahren zur Herstellung von Pyridin-2,3-dicarbonsäurederivaten und neue 1-Amino-1,4-dihydropyridin-2,3-dicarbonsäurederivate |
| EP0172140A2 (de) * | 1984-08-10 | 1986-02-19 | Ciba-Geigy Ag | Verfahren zur Herstellung von Pyridin-2,3-dicarbonsäurederivaten und neue 1-Amino-1,2,3,4-tetrahydropyridin-2,3-dicarbonsäurederivate und 1,4-Dihydropyridin-2,3-dicarbonsäurederivate |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0067511A3 (en) * | 1981-05-19 | 1983-04-06 | Imperial Chemical Industries Plc | Method of inducing tillering using pyridine derivatives, and some of the pyridines themselves, process for preparing them and agricultural compositions containing them |
| BR8502364A (pt) * | 1984-05-21 | 1986-01-21 | American Cyanamid Co | Processo para a preparacao de 2,3-dicarboxilatos de piridina,5-substituidos,6-substituidos e 5,6-dissubstituidos |
| EP0221023A3 (de) * | 1985-10-25 | 1988-11-09 | Ciba-Geigy Ag | Verfahren zur Herstellung von Pyridin-2-carbonsäurederivaten und 1-Amino-1,4-dihydropyridin-2-carbonsäurederivate |
| US4723011A (en) * | 1985-10-28 | 1988-02-02 | American Cyanamid Company | Preparation of substituted and disubstituted-pyridine-2,3-dicarboxylate esters |
-
1986
- 1986-03-10 GB GB868605868A patent/GB8605868D0/en active Pending
-
1987
- 1987-02-11 NL NL8700324A patent/NL8700324A/nl not_active Application Discontinuation
- 1987-03-09 FR FR8703163A patent/FR2595354B1/fr not_active Expired - Fee Related
- 1987-03-09 GB GB8705472A patent/GB2188318B/en not_active Expired - Lifetime
- 1987-03-09 JP JP5224687A patent/JPH0832683B2/ja not_active Expired - Lifetime
- 1987-03-09 DE DE19873707530 patent/DE3707530A1/de not_active Ceased
- 1987-03-09 CH CH87187A patent/CH671762A5/fr not_active IP Right Cessation
- 1987-03-10 BE BE8700229A patent/BE1003158A5/fr not_active IP Right Cessation
-
1995
- 1995-09-12 JP JP7258314A patent/JP2631644B2/ja not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0161221A2 (de) * | 1984-05-11 | 1985-11-13 | Ciba-Geigy Ag | Verfahren zur Herstellung von Pyridin-2,3-dicarbonsäurederivaten und neue 1-Amino-1,4-dihydropyridin-2,3-dicarbonsäurederivate |
| EP0172140A2 (de) * | 1984-08-10 | 1986-02-19 | Ciba-Geigy Ag | Verfahren zur Herstellung von Pyridin-2,3-dicarbonsäurederivaten und neue 1-Amino-1,2,3,4-tetrahydropyridin-2,3-dicarbonsäurederivate und 1,4-Dihydropyridin-2,3-dicarbonsäurederivate |
Non-Patent Citations (1)
| Title |
|---|
| Synthesis(1975), S. 191-192 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996037471A1 (de) * | 1995-05-22 | 1996-11-28 | Basf Aktiengesellschaft | N-aminopyridonderivate und ihre verwendung als herbizide |
| CN108495845A (zh) * | 2016-01-22 | 2018-09-04 | 美国陶氏益农公司 | 制备4-烷氧基-3-乙酰氧基吡啶甲酸的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0832683B2 (ja) | 1996-03-29 |
| GB8605868D0 (en) | 1986-04-16 |
| JPS62212368A (ja) | 1987-09-18 |
| GB8705472D0 (en) | 1987-04-15 |
| FR2595354A1 (fr) | 1987-09-11 |
| GB2188318B (en) | 1990-02-14 |
| NL8700324A (nl) | 1987-10-01 |
| JP2631644B2 (ja) | 1997-07-16 |
| BE1003158A5 (fr) | 1991-12-17 |
| FR2595354B1 (fr) | 1993-11-26 |
| CH671762A5 (enrdf_load_stackoverflow) | 1989-09-29 |
| JPH08198852A (ja) | 1996-08-06 |
| GB2188318A (en) | 1987-09-30 |
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