GB811957A - Improvements relating to 2-hydroxy-4-arylamino-quinolines - Google Patents
Improvements relating to 2-hydroxy-4-arylamino-quinolinesInfo
- Publication number
- GB811957A GB811957A GB6554/57A GB655457A GB811957A GB 811957 A GB811957 A GB 811957A GB 6554/57 A GB6554/57 A GB 6554/57A GB 655457 A GB655457 A GB 655457A GB 811957 A GB811957 A GB 811957A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxy
- quinoline
- quinolines
- anilino
- dihydroxy
- 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.)
- Expired
Links
- 229940111121 antirheumatic drug quinolines Drugs 0.000 title 1
- OYGROUFBUVUVPK-UHFFFAOYSA-N 4-anilino-1h-quinolin-2-one Chemical class C12=CC=CC=C2NC(=O)C=C1NC1=CC=CC=C1 OYGROUFBUVUVPK-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- SDFZIMWRNULDSU-UHFFFAOYSA-N 6-methyl-4-(4-methylanilino)-1H-quinolin-2-one Chemical compound C1(=CC=C(C=C1)NC1=CC(=NC2=CC=C(C=C12)C)O)C SDFZIMWRNULDSU-UHFFFAOYSA-N 0.000 abstract 1
- SDRJFDTZVULXDE-UHFFFAOYSA-N 7-chloro-1h-quinolin-2-one Chemical compound C1=CC(Cl)=CC2=NC(O)=CC=C21 SDRJFDTZVULXDE-UHFFFAOYSA-N 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000003931 anilides Chemical group 0.000 abstract 1
- 150000001555 benzenes Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- FBOFHVFMPNNIKN-UHFFFAOYSA-N dimethylquinoline Natural products C1=CC=C2N=C(C)C(C)=CC2=C1 FBOFHVFMPNNIKN-UHFFFAOYSA-N 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- YYAQOJILQOVUSK-UHFFFAOYSA-N n,n'-diphenylpropanediamide Chemical compound C=1C=CC=CC=1NC(=O)CC(=O)NC1=CC=CC=C1 YYAQOJILQOVUSK-UHFFFAOYSA-N 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 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
-
- 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
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
- C07D215/44—Nitrogen atoms attached in position 4 with aryl radicals attached to said nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Quinoline Compounds (AREA)
Abstract
The invention comprises (1) 2-hydroxy-4-phenylamino-quinolines, the phenyl radical and fused benzene nucleus of which are each substituted by 1 to 3 halogen atoms and/or C1-6 alkyl radicals; and (2) the preparation of these and other 2-hydroxy-4-arylaminoquinolines by heating to at least 250 DEG C. (preferably 270-320 DEG C.) in the presence of aluminium chloride a malonic acid di-anilide in which the anilide groups can be substituted in any position desired except an ortho-position by substituents which do not interfere in the reaction. The products may be isolated by treating the reaction mixture with dilute acid. The examples describe the preparation of 4-anilino-2-hydroxyquinoline, 4 - para - toluidino - 2 - hydroxy - 6 - methylquinoline, 4 - (21:41 - dimethyl - anilino) 2 - hydroxy - 6:8 - dimethylquinoline, 4 - (31 - chloranilino) 2 - hydroxy - 7-chloro - quinoline and 4 - (21:51 - dichloranilino) 2 - hydroxy - 5:8 - dichloro - quinoline. The latter two compounds may be hydrolysed with hot hydrochloric acid to 7-chloro-2:4-dihydroxy - quinoline and 5:8 - dichloro - 2:4-dihydroxy-quinoline, respectively.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH811957X | 1956-03-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB811957A true GB811957A (en) | 1959-04-15 |
Family
ID=4538568
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB6554/57A Expired GB811957A (en) | 1956-03-01 | 1957-02-27 | Improvements relating to 2-hydroxy-4-arylamino-quinolines |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB811957A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1601357A1 (en) * | 2003-03-10 | 2005-12-07 | Schering Corporation | Heterocyclic kinase inhibitors: methods of use and synthesis |
-
1957
- 1957-02-27 GB GB6554/57A patent/GB811957A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1601357A1 (en) * | 2003-03-10 | 2005-12-07 | Schering Corporation | Heterocyclic kinase inhibitors: methods of use and synthesis |
| JP2006519846A (en) * | 2003-03-10 | 2006-08-31 | シェーリング コーポレイション | Heterocyclic kinase inhibitors: methods of use and synthesis |
| EP1601357A4 (en) * | 2003-03-10 | 2007-10-03 | Schering Corp | Heterocyclic kinase inhibitors: methods of use and synthesis |
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