DE275963C - - Google Patents
Info
- Publication number
- DE275963C DE275963C DENDAT275963D DE275963DA DE275963C DE 275963 C DE275963 C DE 275963C DE NDAT275963 D DENDAT275963 D DE NDAT275963D DE 275963D A DE275963D A DE 275963DA DE 275963 C DE275963 C DE 275963C
- Authority
- DE
- Germany
- Prior art keywords
- water
- carboxylic acid
- heated
- methyl
- melting point
- 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.)
- Active
Links
- 150000003839 salts Chemical class 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 150000007513 acids Chemical class 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- -1 aryl Quinoline-4-carboxylic acid Chemical compound 0.000 description 2
- 125000005998 bromoethyl group Chemical group 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- KBBPTHUIJXSWFW-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-ylmethyl)-6-methylquinoline-4-carboxylic acid Chemical compound Cc1ccc2nc(Cc3ccc4OCOc4c3)cc(C(O)=O)c2c1 KBBPTHUIJXSWFW-UHFFFAOYSA-N 0.000 description 1
- BQGFRFCKVQNHEC-UHFFFAOYSA-N 2-methylquinoline-3,4-dicarboxylic acid Chemical compound C1=CC=C2C(C(O)=O)=C(C(O)=O)C(C)=NC2=C1 BQGFRFCKVQNHEC-UHFFFAOYSA-N 0.000 description 1
- QMQXAQUBDPFOSS-UHFFFAOYSA-N 2-phenyl-1h-quinoline-2-carboxylic acid Chemical compound N1C2=CC=CC=C2C=CC1(C(=O)O)C1=CC=CC=C1 QMQXAQUBDPFOSS-UHFFFAOYSA-N 0.000 description 1
- QTHANKFZSPYAPO-UHFFFAOYSA-N 6-methyl-2-phenylquinoline-4-carboxylic acid Chemical compound C1=C(C(O)=O)C2=CC(C)=CC=C2N=C1C1=CC=CC=C1 QTHANKFZSPYAPO-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- VQMSRUREDGBWKT-UHFFFAOYSA-N cinchoninic acid Natural products C1=CC=C2C(C(=O)O)=CC=NC2=C1 VQMSRUREDGBWKT-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
- C07D215/52—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4 with aryl radicals attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE275963C true DE275963C (enrdf_load_stackoverflow) |
Family
ID=532204
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT275963D Active DE275963C (enrdf_load_stackoverflow) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE275963C (enrdf_load_stackoverflow) |
-
0
- DE DENDAT275963D patent/DE275963C/de active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE275963C (enrdf_load_stackoverflow) | ||
| DE668489C (de) | Verfahren zur Darstellung von 2, 4-Dioxo-3, 3-dialkyltetrahydropyridin-6-carbonsaeureestern bzw. der entsprechenden freien Saeuren | |
| DE555004C (de) | Verfahren zur Darstellung von Brenzcatechinarsinsaeuren | |
| DE1039063B (de) | Verfahren zur Herstellung eines antipyretisch wirksamen, substituierten 1, 2-Diphenyl-3, 5-dioxo-pyrazolidins und dessen Salzen | |
| DE2450675C3 (de) | Verfahren zur Herstellung von N-Acyl-4-anilinobuttersäuren und ihren Salzen | |
| DE934103C (de) | Verfahren zur Herstellung von cyclooctylierten Alkylessigsaeuren mit stark gallentreibender Wirkung | |
| DE686243C (de) | Verfahren zur Herstellung von Abkoemmlingen der Pyridin-2, 3-dicarbonsaeure | |
| DE960722C (de) | Verfahren zur Herstellung von Serinen aus Glykokoll und Aldehyden | |
| DE842051C (de) | Verfahren zur Herstellung von Hydrofluoren-2-carbonsaeuren und ihren Derivaten | |
| DE847447C (de) | Verfahren zur Herstellung von 21-Oxypregnen-(5)-ol-(3)-on-(20)-abkoemmlingen | |
| DE1810137C (enrdf_load_stackoverflow) | ||
| DE1000811C2 (de) | Verfahren zur Herstellung von 8-Amino-3-keto-1, 2, 3, 4-tetrahydronaphthalin-1-carbonsaeure, deren N-Acylderivaten, Estern, Salzen und entsprechenden Laktamen | |
| DE959012C (de) | Verfahren zur Herstellung von AEther- bzw. Thioaethercarbonsaeuren | |
| DE881944C (de) | Verfahren zur Herstellung von Cycloalkyloxybenzoylalkyl-bzw. -alkylencarbonsaeuren | |
| DE280000C (enrdf_load_stackoverflow) | ||
| DE1174797B (de) | Verfahren zur Herstellung von Sulfamylanthranilsaeuren | |
| AT257593B (de) | Verfahren zur Herstellung von 1,2,4-Oxadiazol-Derivaten | |
| DE113762C (enrdf_load_stackoverflow) | ||
| DE962886C (de) | Verfahren zur Herstellung von optisch aktiven threo-ª‰, p-Nitrophenylserin-Verbindungen | |
| DE907778C (de) | Verfahren zur Herstellung von N-(2-Formyl-2-ketoaethyl)-N-(arylsulfonyl)-p-aminobenzoyl-Verbindungen | |
| DE958844C (de) | Verfahren zur Herstellung von ª†-Acyl-buttersaeuren | |
| DE439290C (de) | Vefahren zur Herstellung von Naphthooxythiophenen | |
| DE19962346C2 (de) | Verfahren zur Herstellung von in 2-Stellung disubstituierten 1,3-Dioxan-4,6-dionen | |
| AT163640B (de) | Verfahren zur Herstellung eines Salzes einer Chloraryloxyalkylcarbonsäure | |
| DE720160C (de) | Verfahren zur Darstellung von 6-Aminodihydrocinchonin und -dihydrocinchonidin |