CH553783A - Verfahren zur herstellung von chinolinderivaten. - Google Patents
Verfahren zur herstellung von chinolinderivaten.Info
- Publication number
- CH553783A CH553783A CH556267A CH556267A CH553783A CH 553783 A CH553783 A CH 553783A CH 556267 A CH556267 A CH 556267A CH 556267 A CH556267 A CH 556267A CH 553783 A CH553783 A CH 553783A
- Authority
- CH
- Switzerland
- Prior art keywords
- alkyl
- quinoline
- parts
- substd
- benzyloxy
- Prior art date
Links
- 125000000217 alkyl group Chemical group 0.000 title claims abstract description 9
- -1 alkyl quinoline nucleus Chemical group 0.000 title abstract description 35
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title abstract description 6
- 125000003710 aryl alkyl group Chemical group 0.000 title abstract 2
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 10
- 229910052698 phosphorus Inorganic materials 0.000 claims description 10
- 239000011574 phosphorus Substances 0.000 claims description 10
- 150000003248 quinolines Chemical class 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- QLJUIUYIMJNBTP-UHFFFAOYSA-N ethyl 4-oxo-7-phenylmethoxy-6-propoxy-1H-quinoline-3-carboxylate Chemical compound C(C1=CC=CC=C1)OC1=C(C=C2C(=C(C=NC2=C1)C(=O)OCC)O)OCCC QLJUIUYIMJNBTP-UHFFFAOYSA-N 0.000 abstract description 7
- JVXOUTNOZUSOBX-UHFFFAOYSA-N 2-ethyl-7-phenylmethoxy-6-propoxy-1H-quinolin-4-one Chemical compound C(C)C1=NC2=CC(=C(C=C2C(=C1)O)OCCC)OCC1=CC=CC=C1 JVXOUTNOZUSOBX-UHFFFAOYSA-N 0.000 abstract 1
- 208000003495 Coccidiosis Diseases 0.000 abstract 1
- 206010023076 Isosporiasis Diseases 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 28
- 239000000203 mixture Substances 0.000 description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 230000008018 melting Effects 0.000 description 17
- 238000002844 melting Methods 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 150000005637 4-haloquinolines Chemical class 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- UZMWAGQBWWZKSH-UHFFFAOYSA-N CCCOC1=C(C=C(C=C1)NC=C(C(=O)OCC)C(=O)OCC)OCC2=CC=CC=C2 Chemical compound CCCOC1=C(C=C(C=C1)NC=C(C(=O)OCC)C(=O)OCC)OCC2=CC=CC=C2 UZMWAGQBWWZKSH-UHFFFAOYSA-N 0.000 description 4
- NNOPDLNHPOLRRE-UHFFFAOYSA-N Nequinate Chemical compound CCCCC1=CC(C(C(C(=O)OC)=CN2)=O)=C2C=C1OCC1=CC=CC=C1 NNOPDLNHPOLRRE-UHFFFAOYSA-N 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000012265 solid product Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 150000004331 4-hydroxyquinolines Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- WILQKFLSYPDKCC-UHFFFAOYSA-N dimethyl 2-[(4-butyl-3-phenylmethoxyanilino)methylidene]propanedioate Chemical compound CCCCC1=CC=C(NC=C(C(=O)OC)C(=O)OC)C=C1OCC1=CC=CC=C1 WILQKFLSYPDKCC-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- VNZJMWJGRATRTG-UHFFFAOYSA-N methyl 4-oxo-7-phenylmethoxy-1h-quinoline-3-carboxylate Chemical compound C=1C=C2C(=O)C(C(=O)OC)=CNC2=CC=1OCC1=CC=CC=C1 VNZJMWJGRATRTG-UHFFFAOYSA-N 0.000 description 2
- DNIJJUNMFISAFZ-UHFFFAOYSA-N methyl 7-dodecoxy-4-oxo-6-propyl-1H-quinoline-3-carboxylate Chemical compound C(CC)C=1C=C2C(=C(C=NC2=CC1OCCCCCCCCCCCC)C(=O)OC)O DNIJJUNMFISAFZ-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 1
- 241000224483 Coccidia Species 0.000 description 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical group [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 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
- 238000009835 boiling Methods 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- UQYHUQPWRMNKST-UHFFFAOYSA-N ethyl 4-chloro-7-phenylmethoxy-6-propoxyquinoline-3-carboxylate Chemical compound C(C1=CC=CC=C1)OC1=C(C=C2C(=C(C=NC2=C1)C(=O)OCC)Cl)OCCC UQYHUQPWRMNKST-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 229910052736 halogen Chemical group 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- TUJDEASYMVIBDV-UHFFFAOYSA-N methyl 7-[(2,4-dichlorophenyl)methoxy]-4-oxo-6-propyl-1H-quinoline-3-carboxylate Chemical compound ClC1=C(COC2=C(C=C3C(=C(C=NC3=C2)C(=O)OC)O)CCC)C=CC(=C1)Cl TUJDEASYMVIBDV-UHFFFAOYSA-N 0.000 description 1
- VSQBUDAELOTKGK-UHFFFAOYSA-N methyl 7-[(4-chlorophenyl)methoxy]-4-oxo-6-propyl-1H-quinoline-3-carboxylate Chemical compound ClC1=CC=C(COC2=C(C=C3C(=C(C=NC3=C2)C(=O)OC)O)CCC)C=C1 VSQBUDAELOTKGK-UHFFFAOYSA-N 0.000 description 1
- IJIPILXMWHLHMG-UHFFFAOYSA-N methyl 7-[(4-methylphenyl)methoxy]-4-oxo-1H-quinoline-3-carboxylate Chemical compound OC1=C(C=NC2=CC(=CC=C12)OCC1=CC=C(C=C1)C)C(=O)OC IJIPILXMWHLHMG-UHFFFAOYSA-N 0.000 description 1
- VUJXRZMEGYOLOT-UHFFFAOYSA-N methyl 7-[(4-nitrophenyl)methoxy]-4-oxo-1H-quinoline-3-carboxylate Chemical compound OC1=C(C=NC2=CC(=CC=C12)OCC1=CC=C(C=C1)[N+](=O)[O-])C(=O)OC VUJXRZMEGYOLOT-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- QIWNOVRXWQPVIY-UHFFFAOYSA-N propylbenzene Chemical compound [CH2]CCC1=CC=CC=C1 QIWNOVRXWQPVIY-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000007858 starting material Substances 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
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
-
- 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
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Quinoline Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1731566 | 1966-04-20 | ||
| GB1731567 | 1967-03-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH553783A true CH553783A (de) | 1974-09-13 |
Family
ID=26252606
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH556267A CH553783A (de) | 1966-04-20 | 1967-04-19 | Verfahren zur herstellung von chinolinderivaten. |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE697312A (fa) |
| CH (1) | CH553783A (fa) |
| CS (1) | CS160086B2 (fa) |
| DK (1) | DK117768B (fa) |
| ES (1) | ES339542A2 (fa) |
| GB (1) | GB1122435A (fa) |
| NL (1) | NL6705539A (fa) |
| SE (1) | SE369901B (fa) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3472859A (en) * | 1966-11-01 | 1969-10-14 | Sterling Drug Inc | 1-alkyl-1,4-dihydro-4-oxo-3 quinoline-carboxylic acids and esters |
-
1966
- 1966-04-20 GB GB7131566A patent/GB1122435A/en not_active Expired
-
1967
- 1967-04-17 SE SE533167A patent/SE369901B/xx unknown
- 1967-04-19 CS CS286167A patent/CS160086B2/cs unknown
- 1967-04-19 CH CH556267A patent/CH553783A/de not_active IP Right Cessation
- 1967-04-20 DK DK215467A patent/DK117768B/da unknown
- 1967-04-20 NL NL6705539A patent/NL6705539A/xx unknown
- 1967-04-20 BE BE697312D patent/BE697312A/xx unknown
- 1967-04-20 ES ES339542A patent/ES339542A2/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1122435A (en) | 1968-08-07 |
| ES339542A2 (es) | 1968-05-16 |
| BE697312A (fa) | 1967-10-20 |
| DE1695275B1 (de) | 1972-08-31 |
| NL6705539A (fa) | 1967-10-23 |
| SE369901B (fa) | 1974-09-23 |
| DK117768B (da) | 1970-06-01 |
| CS160086B2 (fa) | 1975-02-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |