DE3044904A1 - Fluorierte anthranilsaeure und anthranilsaeurenitril sowie verfahren zu ihrer herstellung - Google Patents
Fluorierte anthranilsaeure und anthranilsaeurenitril sowie verfahren zu ihrer herstellungInfo
- Publication number
- DE3044904A1 DE3044904A1 DE19803044904 DE3044904A DE3044904A1 DE 3044904 A1 DE3044904 A1 DE 3044904A1 DE 19803044904 DE19803044904 DE 19803044904 DE 3044904 A DE3044904 A DE 3044904A DE 3044904 A1 DE3044904 A1 DE 3044904A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- nitrile
- anthranile
- parts
- fluorinated
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 9
- 150000002825 nitriles Chemical class 0.000 title claims description 3
- 239000002253 acid Substances 0.000 title 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 18
- 229910021529 ammonia Inorganic materials 0.000 claims description 9
- -1 6-fluoroanthranilic acid nitrile Chemical class 0.000 claims description 7
- RWZYAGGXGHYGMB-UHFFFAOYSA-N o-aminobenzenecarboxylic acid Natural products NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 6
- BNBRIFIJRKJGEI-UHFFFAOYSA-N 2,6-difluorobenzonitrile Chemical compound FC1=CC=CC(F)=C1C#N BNBRIFIJRKJGEI-UHFFFAOYSA-N 0.000 claims description 5
- RWSFZKWMVWPDGZ-UHFFFAOYSA-N 2-amino-6-fluorobenzoic acid Chemical compound NC1=CC=CC(F)=C1C(O)=O RWSFZKWMVWPDGZ-UHFFFAOYSA-N 0.000 claims description 5
- 150000007514 bases Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 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 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- IQUNZGOZUJITBJ-UHFFFAOYSA-N 2-amino-6-fluorobenzonitrile Chemical compound NC1=CC=CC(F)=C1C#N IQUNZGOZUJITBJ-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-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
- 241000607479 Yersinia pestis Species 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- GRTOGORTSDXSFK-XJTZBENFSA-N ajmalicine Chemical compound C1=CC=C2C(CCN3C[C@@H]4[C@H](C)OC=C([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 GRTOGORTSDXSFK-XJTZBENFSA-N 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803044904 DE3044904A1 (de) | 1980-11-28 | 1980-11-28 | Fluorierte anthranilsaeure und anthranilsaeurenitril sowie verfahren zu ihrer herstellung |
| DE8181108202T DE3161982D1 (en) | 1980-11-28 | 1981-10-12 | Process for preparation of 6-fluoro-anthranilic acid nitrile or 6-fluoro-anthranilic acid and 6-fluoro-anthranilic acid nitrile |
| EP81108202A EP0053247B1 (de) | 1980-11-28 | 1981-10-12 | Verfahren zur Herstellung von 6-Fluor-anthranilsäurenitril oder 6-Fluor-anthranilsäure und 6-Fluor-anthranilsäurenitril |
| US06/318,588 US4359428A (en) | 1980-11-28 | 1981-11-05 | Preparation of fluorinated anthranilic acid and anthranilonitrile |
| JP56182398A JPS57118541A (en) | 1980-11-28 | 1981-11-16 | Manufacture of fluorinated anthranilic acid nitrile |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803044904 DE3044904A1 (de) | 1980-11-28 | 1980-11-28 | Fluorierte anthranilsaeure und anthranilsaeurenitril sowie verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3044904A1 true DE3044904A1 (de) | 1982-07-01 |
Family
ID=6117849
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803044904 Withdrawn DE3044904A1 (de) | 1980-11-28 | 1980-11-28 | Fluorierte anthranilsaeure und anthranilsaeurenitril sowie verfahren zu ihrer herstellung |
| DE8181108202T Expired DE3161982D1 (en) | 1980-11-28 | 1981-10-12 | Process for preparation of 6-fluoro-anthranilic acid nitrile or 6-fluoro-anthranilic acid and 6-fluoro-anthranilic acid nitrile |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8181108202T Expired DE3161982D1 (en) | 1980-11-28 | 1981-10-12 | Process for preparation of 6-fluoro-anthranilic acid nitrile or 6-fluoro-anthranilic acid and 6-fluoro-anthranilic acid nitrile |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4359428A (en, 2012) |
| EP (1) | EP0053247B1 (en, 2012) |
| JP (1) | JPS57118541A (en, 2012) |
| DE (2) | DE3044904A1 (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4504660A (en) * | 1982-07-06 | 1985-03-12 | American Home Products Corporation | Process for the production of 2,6-diaminobenzonitrile derivatives |
| DE3476385D1 (en) * | 1983-09-30 | 1989-03-02 | Basf Ag | Process for the preparation of 5-fluor-4h-3,1-benzoxazin-4-ones |
| US4782179A (en) * | 1987-02-13 | 1988-11-01 | Nippon Shokubai Kagaku Kogyo Co., Ltd. | 3-amino-2,4,5-trifluorobenzoic acid and a method for manufacture thereof |
| US4885386A (en) * | 1988-10-28 | 1989-12-05 | Warner-Lambert Company | Process for the synthesis of 3-chloro-2,4,5-trifluorobenzoic acid |
| GB8919678D0 (en) * | 1989-08-31 | 1989-10-11 | Ici Plc | Fluorobenzene derivatives |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3291790A (en) * | 1962-08-28 | 1966-12-13 | Upjohn Co | Process for preparing dibenzodiazepinone compounds |
| DE1231709B (de) * | 1964-06-20 | 1967-01-05 | Basf Ag | Verfahren zur Herstellung von o-Amino-benzonitrilen |
| SE354062B (en, 2012) * | 1970-06-01 | 1973-02-26 | Bofors Ab | |
| DE2537288A1 (de) * | 1975-08-21 | 1977-03-03 | Bayer Ag | Herstellung von trifluormethylsubstituierten aminobenzonitrilen |
| US4145364A (en) * | 1977-11-30 | 1979-03-20 | Merck & Co., Inc. | Preparation of fluorinated anilines |
| US4178304A (en) * | 1978-03-13 | 1979-12-11 | Efendiev Medzhid R O | Method of producing ortho-aminobenzonitrile |
-
1980
- 1980-11-28 DE DE19803044904 patent/DE3044904A1/de not_active Withdrawn
-
1981
- 1981-10-12 DE DE8181108202T patent/DE3161982D1/de not_active Expired
- 1981-10-12 EP EP81108202A patent/EP0053247B1/de not_active Expired
- 1981-11-05 US US06/318,588 patent/US4359428A/en not_active Expired - Lifetime
- 1981-11-16 JP JP56182398A patent/JPS57118541A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE3161982D1 (en) | 1984-02-23 |
| JPS57118541A (en) | 1982-07-23 |
| US4359428A (en) | 1982-11-16 |
| JPH0136818B2 (en, 2012) | 1989-08-02 |
| EP0053247A1 (de) | 1982-06-09 |
| EP0053247B1 (de) | 1984-01-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |