DE1247324B - Verfahren zur Herstellung von N-(2, 3-Dimethylphenyl)-anthranilsaeure und ihren Salzen - Google Patents
Verfahren zur Herstellung von N-(2, 3-Dimethylphenyl)-anthranilsaeure und ihren SalzenInfo
- Publication number
- DE1247324B DE1247324B DE1963P0031706 DEP0031706A DE1247324B DE 1247324 B DE1247324 B DE 1247324B DE 1963P0031706 DE1963P0031706 DE 1963P0031706 DE P0031706 A DEP0031706 A DE P0031706A DE 1247324 B DE1247324 B DE 1247324B
- Authority
- DE
- Germany
- Prior art keywords
- acid
- dimethylphenyl
- dimethyldiphenylamine
- hydrolysis
- salts
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 20
- HYYBABOKPJLUIN-UHFFFAOYSA-N mefenamic acid Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)C(O)=O)=C1C HYYBABOKPJLUIN-UHFFFAOYSA-N 0.000 title claims description 11
- 150000003839 salts Chemical class 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000002253 acid Substances 0.000 claims description 18
- -1 2,3-dimethylphenyl Chemical group 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 230000007062 hydrolysis Effects 0.000 claims description 7
- 238000006460 hydrolysis reaction Methods 0.000 claims description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
- 239000011707 mineral Substances 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 230000020477 pH reduction Effects 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 235000011167 hydrochloric acid Nutrition 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- OZCVOEUWYVVVME-UHFFFAOYSA-N 2,3-dimethylcyclohexan-1-one Chemical compound CC1CCCC(=O)C1C OZCVOEUWYVVVME-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000005903 acid hydrolysis reaction Methods 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical compound NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000004968 inflammatory condition Effects 0.000 description 2
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OPDUMRSBESYOCQ-UHFFFAOYSA-N 1-(2,3-dimethylphenyl)-3,1-benzoxazine-2,4-dione Chemical compound CC1=CC=CC(N2C(OC(=O)C3=CC=CC=C32)=O)=C1C OPDUMRSBESYOCQ-UHFFFAOYSA-N 0.000 description 1
- VVAKEQGKZNKUSU-UHFFFAOYSA-N 2,3-dimethylaniline Chemical compound CC1=CC=CC(N)=C1C VVAKEQGKZNKUSU-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 208000025747 Rheumatic disease Diseases 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
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000002917 arthritic effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000004656 dimethylamines Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000005171 halobenzenes Chemical class 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- JAVRNIFMYIJXIE-UHFFFAOYSA-N methyl 2-chlorobenzoate Chemical compound COC(=O)C1=CC=CC=C1Cl JAVRNIFMYIJXIE-UHFFFAOYSA-N 0.000 description 1
- 229940102398 methyl anthranilate Drugs 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 150000003956 methylamines Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- BJAARRARQJZURR-UHFFFAOYSA-N trimethylazanium;hydroxide Chemical compound O.CN(C)C BJAARRARQJZURR-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65H—HANDLING THIN OR FILAMENTARY MATERIAL, e.g. SHEETS, WEBS, CABLES
- B65H5/00—Feeding articles separated from piles; Feeding articles to machines
- B65H5/22—Feeding articles separated from piles; Feeding articles to machines by air-blast or suction device
- B65H5/228—Feeding articles separated from piles; Feeding articles to machines by air-blast or suction device by air-blast devices
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65H—HANDLING THIN OR FILAMENTARY MATERIAL, e.g. SHEETS, WEBS, CABLES
- B65H9/00—Registering, e.g. orientating, articles; Devices therefor
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65H—HANDLING THIN OR FILAMENTARY MATERIAL, e.g. SHEETS, WEBS, CABLES
- B65H9/00—Registering, e.g. orientating, articles; Devices therefor
- B65H9/06—Movable stops or gauges, e.g. rising and falling front stops
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA858229 | 1962-09-18 | ||
| CA858222 | 1962-09-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1247324B true DE1247324B (de) | 1967-08-17 |
Family
ID=25673417
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1250446D Pending DE1250446B (de) | 1962-09-18 | Verfahren zur Herstellung von N - (2,3 - Dimethylphenyl) - anthranilsäure und deren Salzen | |
| DE1963P0031706 Pending DE1247324B (de) | 1962-09-18 | 1963-04-30 | Verfahren zur Herstellung von N-(2, 3-Dimethylphenyl)-anthranilsaeure und ihren Salzen |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1250446D Pending DE1250446B (de) | 1962-09-18 | Verfahren zur Herstellung von N - (2,3 - Dimethylphenyl) - anthranilsäure und deren Salzen |
Country Status (6)
| Country | Link |
|---|---|
| BR (2) | BR6348808D0 (cs) |
| CH (2) | CH405346A (cs) |
| DE (2) | DE1247324B (cs) |
| FR (3) | FR1316827A (cs) |
| NL (2) | NL292122A (cs) |
| SE (1) | SE300428B (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3531107A (en) * | 1967-02-28 | 1970-09-29 | Ivanhoe Research Corp | Methods and apparatus for automatically registering fabric workpieces |
-
0
- DE DENDAT1250446D patent/DE1250446B/de active Pending
- NL NL292084D patent/NL292084A/xx unknown
- NL NL292122D patent/NL292122A/xx unknown
-
1962
- 1962-03-02 FR FR889873A patent/FR1316827A/fr not_active Expired
-
1963
- 1963-04-30 BR BR14880863A patent/BR6348808D0/pt unknown
- 1963-04-30 SE SE474963A patent/SE300428B/xx unknown
- 1963-04-30 CH CH540463A patent/CH405346A/fr unknown
- 1963-04-30 FR FR1572109D patent/FR1572109A/fr not_active Expired
- 1963-04-30 DE DE1963P0031706 patent/DE1247324B/de active Pending
- 1963-04-30 BR BR14880163A patent/BR6348801D0/pt unknown
- 1963-04-30 FR FR1572114D patent/FR1572114A/fr not_active Expired
- 1963-04-30 CH CH541363A patent/CH410982A/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL292084A (cs) | |
| BR6348801D0 (pt) | 1973-07-19 |
| CH410982A (fr) | 1966-04-15 |
| CH405346A (fr) | 1966-01-15 |
| BR6348808D0 (pt) | 1973-07-19 |
| FR1316827A (fr) | 1963-02-01 |
| SE300428B (cs) | 1968-04-29 |
| FR1572114A (cs) | 1969-06-27 |
| DE1250446B (de) | 1967-09-21 |
| NL292122A (cs) | |
| FR1572109A (cs) | 1969-06-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1247324B (de) | Verfahren zur Herstellung von N-(2, 3-Dimethylphenyl)-anthranilsaeure und ihren Salzen | |
| DE953256C (de) | Verfahren zur Herstellung von therapeutisch wirksamen bis-[ª-(o-Oxyphenyl)-isopropyl]-aminen | |
| AT209895B (de) | Verfahren zur Herstellung von 3-Amino-2,4,6-trijodbenzoylverbindungen | |
| CH401948A (de) | Verfahren zur Herstellung N-substituierter Phenylsulfonyl-N'-cycloalkylharnstoffe | |
| AT242150B (de) | Verfahren zur Herstellung von neuen, substituierten Dihydrochinoxalonen-(2) sowie von deren Salzen und quaternären Ammoniumverbindungen | |
| CH542179A (de) | Verfahren zur Herstellung des optisch inaktiven oder optisch aktiven N,N'-Bis-(2-(3',4'-dihydroxyphenyl)-2-hydroxyäthyl)-hexamethylendiamins und der Salze desselben | |
| DE1078122B (de) | Verfahren zur Herstellung von 1-Cyclohexylaminoindanen und -aminohydrindanen | |
| DE1235929B (de) | Verfahren zur Herstellung von 2-(2'-Pyrazinyl)-benzimidazol und seinen Salzen | |
| AT238180B (de) | Verfahren zur Herstellung neuer Pyrrolidinverbindungen | |
| AT226710B (de) | Verfahren zur Herstellung von neuen Dihydrochinoxalonen-(2) und von deren Salzen | |
| AT246720B (de) | Verfahren zur Herstellung von neuen cyclischen Aminen und deren Salzen | |
| DE731560C (de) | Verfahren zur Herstellung von basischen Saeureamiden | |
| DE1493828C (de) | Benzamide und Verfahren zu ihrer Herstellung | |
| DE954155C (de) | Verfahren zur Herstellung von 4-Aminochromanen | |
| DE1768818C3 (de) | Anthranilsäureamide und Verfahren zu deren Herstellung | |
| AT232500B (de) | Verfahren zur Herstellung von neuen Phenylalaninderivaten | |
| AT159131B (de) | Verfahren zur Darstellung von in der Aminogruppe basisch substituierten 9-Aminoacridinen. | |
| AT289777B (de) | Verfahren zur Herstellung von neuen heterocyklischen Benzamidderivaten und ihren Salzen | |
| AT213864B (de) | Verfahren zur Herstellung von neuen analgetisch wirksamen α-Amino-β-oxybuttersäureamiden | |
| DE580517C (de) | Verfahren zur UEberfuehrung sekundaerer und tertiaerer Amine in niedere Substitutionsstufen | |
| AT241440B (de) | Verfahren zur Herstellung von N-(2,3-Dimethylphenyl)-anthranilsäure und deren Salzen | |
| CH557815A (de) | Verfahren zur herstellung von 3-indol-aliphatischen saeuren. | |
| AT311968B (de) | Verfahren zur Herstellung von neuen heterocyclischen Aminophenylalkylaminen sowie von deren Säureadditionssalzen | |
| AT257604B (de) | Verfahren zur Herstellung neuer substituierter Diaminopyridine | |
| AT238167B (de) | Verfahren zur Herstellung von N-(2,3-Dimethylphenyl)-anthranilsäure und deren Salzen |