CH572471A5 - 4-Methyl-7-substd.-2(1H)-quinolones prepn. - by reacting 1,3-phenylenediamine with diketene - Google Patents

4-Methyl-7-substd.-2(1H)-quinolones prepn. - by reacting 1,3-phenylenediamine with diketene

Info

Publication number: CH572471A5
Authority: CH; Switzerland
Prior art keywords: acetic acid; diketene; phenylenediamine; methyl; reaction
Prior art date: 1973-09-20

Application number

CH1349273A

Other languages

German (de)

English (en)

Original Assignee

Lonza Ag

Priority date (The priority date 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 date listed.)

1973-09-20

Filing date

1973-09-20

Publication date

1976-02-13

1973-09-20 Application filed by Lonza Ag filed Critical Lonza Ag

1973-09-20 Priority to CH1349273A priority Critical patent/CH572471A5/de

1974-09-12 Priority to JP10590474A priority patent/JPS5058080A/ja

1974-09-13 Priority to GB4001374A priority patent/GB1420530A/en

1974-09-16 Priority to CS633874A priority patent/CS182266B2/cs

1974-09-18 Priority to IT5307374A priority patent/IT1035085B/it

1974-09-18 Priority to DE19742444519 priority patent/DE2444519C2/de

1974-09-18 Priority to DD18117974A priority patent/DD113536A5/xx

1974-09-20 Priority to BE148752A priority patent/BE820170A/fr

1974-09-20 Priority to CA209,659A priority patent/CA1042894A/fr

1974-09-20 Priority to NL7412463A priority patent/NL7412463A/xx

1974-09-20 Priority to AT759274A priority patent/AT337184B/de

1974-09-20 Priority to FR7431844A priority patent/FR2244763B1/fr

1974-09-20 Priority to LU70958A priority patent/LU70958A1/xx

1975-03-14 Priority to US05/558,355 priority patent/US4064131A/en

1976-02-13 Publication of CH572471A5 publication Critical patent/CH572471A5/de

Links

WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 title claims abstract description 14
WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 title claims abstract description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 50
229960000583 acetic acid Drugs 0.000 claims description 16
238000000034 method Methods 0.000 claims description 16
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 claims description 8
229940018564 m-phenylenediamine Drugs 0.000 claims description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
238000010992 reflux Methods 0.000 claims description 6
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims description 4
239000012362 glacial acetic acid Substances 0.000 claims description 4
238000002844 melting Methods 0.000 claims description 4
230000008018 melting Effects 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
MEWHVQCJPFDWIO-UHFFFAOYSA-N 4-methylquinolin-7-amine Chemical compound NC1=CC=C2C(C)=CC=NC2=C1 MEWHVQCJPFDWIO-UHFFFAOYSA-N 0.000 claims description 2
WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims description 2
-1 Acetoacetic acid ester Chemical class 0.000 claims description 2
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 2
239000003054 catalyst Substances 0.000 claims description 2
150000001875 compounds Chemical class 0.000 claims description 2
238000001816 cooling Methods 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
239000012450 pharmaceutical intermediate Substances 0.000 claims description 2
239000007858 starting material Substances 0.000 claims description 2
239000003814 drug Substances 0.000 abstract 1
239000000049 pigment Substances 0.000 abstract 1
150000007660 quinolones Chemical class 0.000 abstract 1
239000002904 solvent Substances 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
- C07D215/38—Nitrogen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Quinoline Compounds (AREA)

CH1349273A 1973-09-20 1973-09-20 4-Methyl-7-substd.-2(1H)-quinolones prepn. - by reacting 1,3-phenylenediamine with diketene CH572471A5 (en)

Priority Applications (14)

Application Number	Priority Date	Filing Date	Title
CH1349273A CH572471A5 (en)	1973-09-20	1973-09-20	4-Methyl-7-substd.-2(1H)-quinolones prepn. - by reacting 1,3-phenylenediamine with diketene
JP10590474A JPS5058080A (fr)	1973-09-20	1974-09-12
GB4001374A GB1420530A (en)	1973-09-20	1974-09-13	Process for preparing quinoline derivatives
CS633874A CS182266B2 (en)	1973-09-20	1974-09-16	Method of producing 1,2-dihydro-2-oxo-4-methyl-7-nh-r-quinoline
IT5307374A IT1035085B (it)	1973-09-20	1974-09-18	Prodedimento per la produzione di composti chinilinici
DE19742444519 DE2444519C2 (de)	1973-09-20	1974-09-18	Verfahren zur Herstellung von 1,2-Dihydro-2-oxo-4-methyl-chinolin-Derivaten
DD18117974A DD113536A5 (fr)	1973-09-20	1974-09-18
BE148752A BE820170A (fr)	1973-09-20	1974-09-20	Procede de preparation de 1
CA209,659A CA1042894A (fr)	1973-09-20	1974-09-20	Procede de fabrication de la dihydro,1.2-oxo,2-methyle,4-amino,7-quinoleine et d'un compose connexe
NL7412463A NL7412463A (nl)	1973-09-20	1974-09-20	Werkwijze voor de bereiding van 1,2-dihydro-2- -oxo-4-methyl-7-aminochinoline alsmede van 1,2-dihydro-2-oxo-4-methyl-7-acetazijnzuur- -amidochinoline.
AT759274A AT337184B (de)	1973-09-20	1974-09-20	Verfahren zur herstellung von 1,2-dihydro-2-oxo-4-methyl-7-amino-chinolin und des neuen 1,2-dihydro-2-oxo-4-methyl-7-acetoacetylamino-chinolins
FR7431844A FR2244763B1 (fr)	1973-09-20	1974-09-20
LU70958A LU70958A1 (fr)	1973-09-20	1974-09-20
US05/558,355 US4064131A (en)	1973-09-20	1975-03-14	Process for the production of 1,2-dihydro-2-oxo-4-methyl-7-acetoacetic acid amido-quinoline

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
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
CH572471A5 true CH572471A5 (en)	1976-02-13

Family

ID=4392915

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1349273A CH572471A5 (en)	1973-09-20	1973-09-20	4-Methyl-7-substd.-2(1H)-quinolones prepn. - by reacting 1,3-phenylenediamine with diketene

Country Status (2)

Country	Link
BE (1)	BE820170A (fr)
CH (1)	CH572471A5 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1135441A (fr) *	1979-11-09	1982-11-09	Polysar Limited	Membrane

1973
- 1973-09-20 CH CH1349273A patent/CH572471A5/de not_active IP Right Cessation
1974
- 1974-09-20 BE BE148752A patent/BE820170A/fr unknown

Also Published As

Publication number	Publication date
BE820170A (fr)	1975-03-20

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Legal Events

Date	Code	Title	Description
1984-05-30	PL	Patent ceased
2024-10-31	PL	Patent ceased