DE2444519C2 - Verfahren zur Herstellung von 1,2-Dihydro-2-oxo-4-methyl-chinolin-Derivaten - Google Patents
Verfahren zur Herstellung von 1,2-Dihydro-2-oxo-4-methyl-chinolin-DerivatenInfo
- Publication number
- DE2444519C2 DE2444519C2 DE19742444519 DE2444519A DE2444519C2 DE 2444519 C2 DE2444519 C2 DE 2444519C2 DE 19742444519 DE19742444519 DE 19742444519 DE 2444519 A DE2444519 A DE 2444519A DE 2444519 C2 DE2444519 C2 DE 2444519C2
- Authority
- DE
- Germany
- Prior art keywords
- dihydro
- oxo
- methyl
- preparation
- acetic acid
- 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
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 3
- APLVPBUBDFWWAD-UHFFFAOYSA-N 4-methylquinolin-2(1H)-one Chemical class C1=CC=C2C(C)=CC(=O)NC2=C1 APLVPBUBDFWWAD-UHFFFAOYSA-N 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
- 229960000583 acetic acid Drugs 0.000 description 11
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 8
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 229940018564 m-phenylenediamine Drugs 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- MJXYFLJHTUSJGU-UHFFFAOYSA-N 7-amino-4-methyl-1h-quinolin-2-one Chemical compound NC1=CC=C2C(C)=CC(=O)NC2=C1 MJXYFLJHTUSJGU-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940120503 dihydroxyacetone Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 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
- C07D215/38—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1349373A CH577973A5 (en) | 1973-09-20 | 1973-09-20 | 4-Methyl-7-substd.-2(1H)-quinolones prepn. - by reacting 1,3-phenylenediamine with diketene |
| CH1349273A CH572471A5 (en) | 1973-09-20 | 1973-09-20 | 4-Methyl-7-substd.-2(1H)-quinolones prepn. - by reacting 1,3-phenylenediamine with diketene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2444519A1 DE2444519A1 (de) | 1975-03-27 |
| DE2444519C2 true DE2444519C2 (de) | 1982-08-26 |
Family
ID=25712387
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742444519 Expired DE2444519C2 (de) | 1973-09-20 | 1974-09-18 | Verfahren zur Herstellung von 1,2-Dihydro-2-oxo-4-methyl-chinolin-Derivaten |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5058080A (enExample) |
| AT (1) | AT337184B (enExample) |
| CA (1) | CA1042894A (enExample) |
| CS (1) | CS182266B2 (enExample) |
| DD (1) | DD113536A5 (enExample) |
| DE (1) | DE2444519C2 (enExample) |
| FR (1) | FR2244763B1 (enExample) |
| GB (1) | GB1420530A (enExample) |
| IT (1) | IT1035085B (enExample) |
| LU (1) | LU70958A1 (enExample) |
| NL (1) | NL7412463A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100374423C (zh) * | 2001-12-11 | 2008-03-12 | 西巴特殊化学品控股有限公司 | 4-甲基-7-氨基喹诺酮的制备工艺 |
-
1974
- 1974-09-12 JP JP10590474A patent/JPS5058080A/ja active Pending
- 1974-09-13 GB GB4001374A patent/GB1420530A/en not_active Expired
- 1974-09-16 CS CS633874A patent/CS182266B2/cs unknown
- 1974-09-18 IT IT5307374A patent/IT1035085B/it active
- 1974-09-18 DE DE19742444519 patent/DE2444519C2/de not_active Expired
- 1974-09-18 DD DD18117974A patent/DD113536A5/xx unknown
- 1974-09-20 NL NL7412463A patent/NL7412463A/xx not_active Application Discontinuation
- 1974-09-20 FR FR7431844A patent/FR2244763B1/fr not_active Expired
- 1974-09-20 CA CA209,659A patent/CA1042894A/en not_active Expired
- 1974-09-20 AT AT759274A patent/AT337184B/de not_active IP Right Cessation
- 1974-09-20 LU LU70958A patent/LU70958A1/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7412463A (nl) | 1975-03-24 |
| DD113536A5 (enExample) | 1975-06-12 |
| AT337184B (de) | 1977-06-10 |
| CS182266B2 (en) | 1978-04-28 |
| JPS5058080A (enExample) | 1975-05-20 |
| GB1420530A (en) | 1976-01-07 |
| DE2444519A1 (de) | 1975-03-27 |
| FR2244763A1 (enExample) | 1975-04-18 |
| LU70958A1 (enExample) | 1975-05-28 |
| ATA759274A (de) | 1976-10-15 |
| CA1042894A (en) | 1978-11-21 |
| FR2244763B1 (enExample) | 1979-03-16 |
| IT1035085B (it) | 1979-10-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE60310554T2 (de) | Verfahren zur herstellung von chinolinderivaten | |
| DE3147276A1 (de) | Verfahren zur herstellung von indolderivaten, deren verwendung als wertvolle zwischenprodukte und neue 4-hydroxyindole | |
| DE2444519C2 (de) | Verfahren zur Herstellung von 1,2-Dihydro-2-oxo-4-methyl-chinolin-Derivaten | |
| DE3840554A1 (de) | Verfahren zur herstellung von pyridin-2,3-dicarbonsaeureestern | |
| EP0124041A1 (de) | Verfahren zur Herstellung von Cyclohexandionderivaten | |
| DE2347015A1 (de) | Neue pyrazolyloxyessigsaeurederivate und verfahren zu ihrer herstellung | |
| DE2264413C2 (enExample) | ||
| EP0004535B1 (de) | Verfahren zur Herstellung von 4-Methyl-5-((2-aminoäthyl)-thiomethyl)-imidazol-dihydrochlorid | |
| DE2406972C3 (de) | Verfahren zur Herstellung von 5-Sulfamoylanthranilsäuren | |
| CH572471A5 (en) | 4-Methyl-7-substd.-2(1H)-quinolones prepn. - by reacting 1,3-phenylenediamine with diketene | |
| DE2636722A1 (de) | 3-hydroxy-pyrrolinon-2-derivate | |
| DE68929429T2 (de) | Verfahren zur Herstellung von Pyridin-2,3-Dicarbonsäure-Verbindungen | |
| EP0206294B1 (de) | 3-Hydroxy-3-(2-Methyl-5-pyridyl)-propionsäurealkylester | |
| CH577973A5 (en) | 4-Methyl-7-substd.-2(1H)-quinolones prepn. - by reacting 1,3-phenylenediamine with diketene | |
| DE946899C (de) | Verfahren zur Herstellung von 5-Pregnen-3, 17ª‡-diol-20-on | |
| DE2360407A1 (de) | Herstellung von omega-amino-betaalkoxycarbonsauren estern | |
| DE2260859A1 (de) | Verfahren zur herstellung von 2,3,4,5,6, 7-hexahydrocyclopenta eckige klammer auf e eckige klammer zu -1,3-oxazin-2,4-dionen | |
| DE1543995C (de) | Verfahren zur Herstellung von 5 (3 see AminoalkyhdenH0,11 dihydro 5H dibenzo eckige Klammer auf a,d ecki ge Klammer zu cycloheptenen | |
| DE2222833A1 (de) | Cyclopenteno-chinolonderivate und verfahren zur herstellung derselben | |
| DE1044818B (de) | Verfahren zur Herstellung von 2substituierten 4, 5-Dihydro-ª‰-carbolinen | |
| DE1595952A1 (de) | Verfahren zur Herstellung von 5-Chlor-3-aminopyrazinoaten | |
| DE2003680A1 (de) | Benzilsaeurederivate | |
| DE1300940B (de) | Verfahren zur Herstellung von Tetrahydropyranylaethern von Steroiden | |
| DE2206424A1 (de) | Verfahren zur Herstellung von N-substituierten Anthranilsäurederivaten | |
| DE1213841B (de) | Verfahren zur Herstellung von 3-Aryl-4-halogen-pyridazonen-(6) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |