CA1042894A - Process for the production of 1,2-dihydro-2-oxo-4-methyl-7-amino-quinoline and a related compound - Google Patents
Process for the production of 1,2-dihydro-2-oxo-4-methyl-7-amino-quinoline and a related compoundInfo
- Publication number
- CA1042894A CA1042894A CA209,659A CA209659A CA1042894A CA 1042894 A CA1042894 A CA 1042894A CA 209659 A CA209659 A CA 209659A CA 1042894 A CA1042894 A CA 1042894A
- Authority
- CA
- Canada
- Prior art keywords
- acetic acid
- mole
- reaction
- diketene
- dihydro
- 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 abstract description 28
- 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 title claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 title 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims abstract description 22
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229940018564 m-phenylenediamine Drugs 0.000 claims abstract description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 89
- 229960000583 acetic acid Drugs 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 239000003960 organic solvent Substances 0.000 claims description 12
- 230000003197 catalytic effect Effects 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- 238000010992 reflux Methods 0.000 claims description 8
- 239000012362 glacial acetic acid Substances 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims 1
- GCMNJUJAKQGROZ-UHFFFAOYSA-N 1,2-Dihydroquinolin-2-imine Chemical compound C1=CC=CC2=NC(N)=CC=C21 GCMNJUJAKQGROZ-UHFFFAOYSA-N 0.000 abstract 1
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- -1 amido quinoline Chemical compound 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 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
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003814 drug Substances 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
- 239000000049 pigment Substances 0.000 description 1
- 239000002904 solvent 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
- C07D215/38—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (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 (1)
| Publication Number | Publication Date |
|---|---|
| CA1042894A true CA1042894A (en) | 1978-11-21 |
Family
ID=25712387
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA209,659A Expired CA1042894A (en) | 1973-09-20 | 1974-09-20 | Process for the production of 1,2-dihydro-2-oxo-4-methyl-7-amino-quinoline and a related compound |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5058080A (cs) |
| AT (1) | AT337184B (cs) |
| CA (1) | CA1042894A (cs) |
| CS (1) | CS182266B2 (cs) |
| DD (1) | DD113536A5 (cs) |
| DE (1) | DE2444519C2 (cs) |
| FR (1) | FR2244763B1 (cs) |
| GB (1) | GB1420530A (cs) |
| IT (1) | IT1035085B (cs) |
| LU (1) | LU70958A1 (cs) |
| NL (1) | NL7412463A (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005518373A (ja) * | 2001-12-11 | 2005-06-23 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | ４−メチル−７−アミノキノロンの製造方法 |
-
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 DD DD18117974A patent/DD113536A5/xx unknown
- 1974-09-18 DE DE19742444519 patent/DE2444519C2/de not_active Expired
- 1974-09-18 IT IT5307374A patent/IT1035085B/it active
- 1974-09-20 FR FR7431844A patent/FR2244763B1/fr not_active Expired
- 1974-09-20 AT AT759274A patent/AT337184B/de not_active IP Right Cessation
- 1974-09-20 NL NL7412463A patent/NL7412463A/xx not_active Application Discontinuation
- 1974-09-20 CA CA209,659A patent/CA1042894A/en not_active Expired
- 1974-09-20 LU LU70958A patent/LU70958A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS182266B2 (en) | 1978-04-28 |
| NL7412463A (nl) | 1975-03-24 |
| AT337184B (de) | 1977-06-10 |
| IT1035085B (it) | 1979-10-20 |
| LU70958A1 (cs) | 1975-05-28 |
| GB1420530A (en) | 1976-01-07 |
| JPS5058080A (cs) | 1975-05-20 |
| ATA759274A (de) | 1976-10-15 |
| FR2244763B1 (cs) | 1979-03-16 |
| DE2444519C2 (de) | 1982-08-26 |
| FR2244763A1 (cs) | 1975-04-18 |
| DE2444519A1 (de) | 1975-03-27 |
| DD113536A5 (cs) | 1975-06-12 |
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