DE2227743C3 - Verfahre« zur Herstellung von 8-Hydroxy-l,3-dioxolo eckige Klammer auf 4,5-g eckige Klammer zu chinolin-7carbonsäureäthylester - Google Patents
Verfahre« zur Herstellung von 8-Hydroxy-l,3-dioxolo eckige Klammer auf 4,5-g eckige Klammer zu chinolin-7carbonsäureäthylesterInfo
- Publication number
- DE2227743C3 DE2227743C3 DE19722227743 DE2227743A DE2227743C3 DE 2227743 C3 DE2227743 C3 DE 2227743C3 DE 19722227743 DE19722227743 DE 19722227743 DE 2227743 A DE2227743 A DE 2227743A DE 2227743 C3 DE2227743 C3 DE 2227743C3
- Authority
- DE
- Germany
- Prior art keywords
- square brackets
- reaction mixture
- hydroxy
- dioxolo
- temperature
- 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
- 238000004519 manufacturing process Methods 0.000 title description 3
- PPZOEUCJAYRMHY-UHFFFAOYSA-N ethyl quinoline-7-carboxylate Chemical compound C1=CC=NC2=CC(C(=O)OCC)=CC=C21 PPZOEUCJAYRMHY-UHFFFAOYSA-N 0.000 title 1
- 238000000034 method Methods 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 8
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- 230000008901 benefit Effects 0.000 description 4
- 239000011928 denatured alcohol Substances 0.000 description 4
- -1 diethyl (3,4 - methylenedioxyphenyl) aminomethylene Chemical group 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 3
- VZKWWMFVWHSLHK-UHFFFAOYSA-N ethyl 8-oxo-5h-[1,3]dioxolo[4,5-g]quinoline-7-carboxylate Chemical compound C1=C2C(=O)C(C(=O)OCC)=CNC2=CC2=C1OCO2 VZKWWMFVWHSLHK-UHFFFAOYSA-N 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- KYGZCKSPAKDVKC-UHFFFAOYSA-N Oxolinic acid Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC2=C1OCO2 KYGZCKSPAKDVKC-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- YATKGRDNKXAXJG-UHFFFAOYSA-N diethyl 2-[amino(1,3-benzodioxol-5-yl)methylidene]propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)=C(N)C1=CC=C2OCOC2=C1 YATKGRDNKXAXJG-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229960000321 oxolinic acid Drugs 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- DJDDYWYYTKNZPM-UHFFFAOYSA-N 2-amino-1,3-dioxane-4,6-dione Chemical compound NC1OC(=O)CC(=O)O1 DJDDYWYYTKNZPM-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- LTEOHQLUJPPHMP-UHFFFAOYSA-N C(C)O.[P] Chemical compound C(C)O.[P] LTEOHQLUJPPHMP-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- WXXVQWSDMOAHHV-UHFFFAOYSA-N quinoline-7-carboxylic acid Chemical compound C1=CC=NC2=CC(C(=O)O)=CC=C21 WXXVQWSDMOAHHV-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
- C07D317/66—Nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16445171A | 1971-07-20 | 1971-07-20 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2227743A1 DE2227743A1 (de) | 1973-02-08 |
| DE2227743B2 DE2227743B2 (de) | 1974-02-21 |
| DE2227743C3 true DE2227743C3 (de) | 1974-10-03 |
Family
ID=22594538
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722227743 Expired DE2227743C3 (de) | 1971-07-20 | 1972-06-07 | Verfahre« zur Herstellung von 8-Hydroxy-l,3-dioxolo eckige Klammer auf 4,5-g eckige Klammer zu chinolin-7carbonsäureäthylester |
Country Status (8)
| Country | Link |
|---|---|
| AU (1) | AU466435B2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA966135A (cg-RX-API-DMAC7.html) |
| DE (1) | DE2227743C3 (cg-RX-API-DMAC7.html) |
| FI (1) | FI50973C (cg-RX-API-DMAC7.html) |
| FR (1) | FR2146779A5 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1337377A (cg-RX-API-DMAC7.html) |
| NO (1) | NO134987C (cg-RX-API-DMAC7.html) |
| SE (1) | SE394437B (cg-RX-API-DMAC7.html) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4284777A (en) * | 1978-12-26 | 1981-08-18 | E. I. Du Pont De Nemours And Company | Antibacterials: 1-difluoromethyl-6,7-methylenedioxy-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid and its esters |
-
1972
- 1972-06-07 FI FI161372A patent/FI50973C/fi active
- 1972-06-07 DE DE19722227743 patent/DE2227743C3/de not_active Expired
- 1972-06-21 CA CA145,330A patent/CA966135A/en not_active Expired
- 1972-06-26 GB GB2984772A patent/GB1337377A/en not_active Expired
- 1972-07-10 AU AU44412/72A patent/AU466435B2/en not_active Expired
- 1972-07-14 SE SE934672A patent/SE394437B/xx unknown
- 1972-07-17 FR FR7225683A patent/FR2146779A5/fr not_active Expired
- 1972-07-19 NO NO259172A patent/NO134987C/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA966135A (en) | 1975-04-15 |
| AU466435B2 (en) | 1975-10-30 |
| DE2227743B2 (de) | 1974-02-21 |
| NO134987B (cg-RX-API-DMAC7.html) | 1976-10-11 |
| SE394437B (sv) | 1977-06-27 |
| FI50973C (fi) | 1976-09-10 |
| GB1337377A (en) | 1973-11-14 |
| FI50973B (cg-RX-API-DMAC7.html) | 1976-05-31 |
| AU4441272A (en) | 1974-01-17 |
| FR2146779A5 (cg-RX-API-DMAC7.html) | 1973-03-02 |
| NO134987C (cg-RX-API-DMAC7.html) | 1977-01-19 |
| DE2227743A1 (de) | 1973-02-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8328 | Change in the person/name/address of the agent |
Free format text: HENKEL, G., DR.PHIL. FEILER, L., DR.RER.NAT., PAT.-ANW., 8000 MUENCHEN |