CH524604A - Verfahren zur Herstellung von Chinolin-Derivaten - Google Patents

Verfahren zur Herstellung von Chinolin-Derivaten

Info

Publication number: CH524604A
Authority: CH; Switzerland
Prior art keywords: formula; methylenedioxy; carried out; hydrolysis; dependent
Prior art date: 1969-04-26

Application number

CH595470A

Other languages

German (de)

English (en)

Inventor

Zoltan Dr Meszaros

Peter Dr Szentmiklosi

Frank Judit

Csaszar Janos

Gyorgy Dr Kormoczy

Original Assignee

Chinoin Gyogyszer Es Vegyeszet

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.)

1969-04-26

Filing date

1970-04-21

Publication date

1972-06-30

1970-04-21 Application filed by Chinoin Gyogyszer Es Vegyeszet filed Critical Chinoin Gyogyszer Es Vegyeszet

1972-06-30 Publication of CH524604A publication Critical patent/CH524604A/de

Links

230000007062 hydrolysis Effects 0.000 title claims description 10
238000006460 hydrolysis reaction Methods 0.000 title claims description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 20
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 14
150000003839 salts Chemical class 0.000 claims abstract description 13
DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 claims abstract description 9
DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 claims abstract description 8
125000000217 alkyl group Chemical group 0.000 claims abstract description 7
239000003795 chemical substances by application Substances 0.000 claims abstract description 7
-1 methylenedioxy Chemical group 0.000 claims abstract description 7
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 4
229910052736 halogen Inorganic materials 0.000 claims abstract description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 3
125000005843 halogen group Chemical group 0.000 claims abstract 2
238000000034 method Methods 0.000 claims description 17
150000001875 compounds Chemical class 0.000 claims description 15
239000011541 reaction mixture Substances 0.000 claims description 9
229940008406 diethyl sulfate Drugs 0.000 claims description 6
238000005956 quaternization reaction Methods 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
238000009835 boiling Methods 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
239000012429 reaction media Substances 0.000 claims description 2
239000007858 starting material Substances 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 4
125000004429 atom Chemical group 0.000 abstract 1
235000019253 formic acid Nutrition 0.000 abstract 1
230000003301 hydrolyzing effect Effects 0.000 abstract 1
238000002955 isolation Methods 0.000 abstract 1
239000000047 product Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 5
239000002253 acid Substances 0.000 description 4
239000003610 charcoal Substances 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
150000008044 alkali metal hydroxides Chemical class 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
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
150000007513 acids Chemical class 0.000 description 2
238000004140 cleaning Methods 0.000 description 2
IQDOHPSCFUSFGJ-UHFFFAOYSA-N ethyl 8-chloro-[1,3]dioxolo[4,5-g]quinoline-7-carboxylate Chemical compound C1=C2OCOC2=CC2=C(Cl)C(C(=O)OCC)=CN=C21 IQDOHPSCFUSFGJ-UHFFFAOYSA-N 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
239000002609 medium Substances 0.000 description 2
239000000155 melt Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000006798 ring closing metathesis reaction Methods 0.000 description 2
XGNXYCFREOZBOL-UHFFFAOYSA-N 1,3-benzodioxol-5-amine Chemical compound NC1=CC=C2OCOC2=C1 XGNXYCFREOZBOL-UHFFFAOYSA-N 0.000 description 1
ZSEJADLCFCHIGX-UHFFFAOYSA-N 1-ethyl-4-oxoquinoline-3-carboxylic acid Chemical compound C1=CC=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 ZSEJADLCFCHIGX-UHFFFAOYSA-N 0.000 description 1
SNHCYVGJJIKKNG-UHFFFAOYSA-N 8-oxo-5h-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid Chemical compound C1=C2C(=O)C(C(=O)O)=CNC2=CC2=C1OCO2 SNHCYVGJJIKKNG-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
230000002411 adverse Effects 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000001804 chlorine Chemical class 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
150000008050 dialkyl sulfates Chemical class 0.000 description 1
LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
DWXQUAHMZWZXHP-UHFFFAOYSA-N ethyl 4-chloroquinoline-3-carboxylate Chemical compound C1=CC=CC2=C(Cl)C(C(=O)OCC)=CN=C21 DWXQUAHMZWZXHP-UHFFFAOYSA-N 0.000 description 1
229960003750 ethyl chloride Drugs 0.000 description 1
230000006203 ethylation Effects 0.000 description 1
238000006200 ethylation reaction Methods 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
125000001183 hydrocarbyl group Chemical group 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 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
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003248 quinolines Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-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
- 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)
Electroluminescent Light Sources (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH595470A 1969-04-26 1970-04-21 Verfahren zur Herstellung von Chinolin-Derivaten CH524604A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HUCI000887		1969-04-26

Publications (1)

Publication Number	Publication Date
CH524604A true CH524604A (de)	1972-06-30

Family

ID=10994364

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH595470A CH524604A (de)	1969-04-26	1970-04-21	Verfahren zur Herstellung von Chinolin-Derivaten

Country Status (6)

Country	Link
AT (1)	AT296990B (da)
CH (1)	CH524604A (da)
DK (1)	DK132323C (da)
FI (1)	FI49500C (da)
NO (1)	NO134156C (da)
SE (1)	SE393806B (da)

1970
- 1970-04-21 CH CH595470A patent/CH524604A/de not_active IP Right Cessation
- 1970-04-21 SE SE550170A patent/SE393806B/xx unknown
- 1970-04-21 NO NO150870A patent/NO134156C/no unknown
- 1970-04-23 DK DK206370A patent/DK132323C/da active
- 1970-04-24 AT AT375870A patent/AT296990B/de not_active IP Right Cessation
- 1970-04-24 FI FI115770A patent/FI49500C/fi active

Also Published As

Publication number	Publication date
NO134156C (da)	1976-08-25
SE393806B (sv)	1977-05-23
DK132323C (da)	1976-04-26
DK132323B (da)	1975-11-24
NO134156B (da)	1976-05-18
AT296990B (de)	1972-03-10
FI49500C (fi)	1975-07-10
FI49500B (da)	1975-04-01

Legal Events

Date	Code	Title	Description
1978-12-15	PL	Patent ceased

Publication	Publication Date	Title
DE2345302A1 (de)	1974-03-21	Aufspaltung von optisch aktiven verbindungen
DD269848A5 (de)	1989-07-12	Verfahren zur herstellung von chinolincarbonsaeure
AT200578B (de)	1958-11-10	Verfahren zur Herstellung von neuen N-Aminoalkylderivaten von Azepinen
CH415661A (de)	1966-06-30	Verfahren zur Herstellung von N-Alkoxy-B-phenyl-äthylaminen
CH524604A (de)	1972-06-30	Verfahren zur Herstellung von Chinolin-Derivaten
EP0067352B1 (de)	1984-08-15	Verfahren zur Herstellung von S-Aryl-thioglycolsäuren
DE2613172A1 (de)	1977-10-06	Verfahren zur herstellung von penicillinen und cephalosporinen
DE830511C (de)	1952-02-04	Verfahren zur Herstellung von neuen diquartaeren Salzen von Pyrimidylaminochinolinen
DE1695549C3 (de)	1974-05-09	Verfahren zur Herstellung von LundDL-alpha-Methyl-3,4-dihydroxyphenylalanin
DE737796C (de)	1943-07-24	Verfahren zur Herstellung neuer p-Aminobenzolsulfonamidverbindungen
DE1801205A1 (de)	1969-08-28	Aminoalkylierte Thioaether von 2-Mercaptoindolen und Verfahren zu ihrer Herstellung
DE855706C (de)	1952-11-17	Verfahren zur Herstellung von Abkoemmlingen des 4, 4'-Diaminostilbens
DE1470424C (de)	1972-11-02	Verfahren zur Herstellung von 3-Alkylthiazolidin-4-onen
AT339326B (de)	1977-10-10	Verfahren zur herstellung von 1,8-naphthyridin -3- carbonsauren
DE2711363A1 (de)	1978-09-21	Verfahren zur herstellung von sulfonierten benzofuran-derivaten
DE749975C (de)	1945-01-09	Verfahren zur Herstellung von N-Acetoacetylabkoemmlingen von Aminoverbindungen
DE1902583A1 (de)	1969-08-28	Verfahren zur Herstellung von Benzoesaeurederivaten
CH536315A (de)	1973-04-30	Verfahren zur Herstellung von neuen Chinolin-Derivaten
AT206896B (de)	1959-12-28	Verfahren zur Herstellung von neuen racemischen oder optisch aktiven Morpholinderivaten und ihren Salzen
AT204554B (de)	1959-07-25	Verfahren zur Herstellung von N-Alkyl-α-piperidincarbonsäureaniliden
AT367394B (de)	1982-06-25	Verfahren zur herstellung neuer indanderivate
DE1493854C (de)	1971-12-30	Benzanilide und Verfahren zu ihrer Herstellung
AT243801B (de)	1965-12-10	Verfahren zur Herstellung von neuen, im Pyridinring durch ein Halogenatom substituierten 4-Azaphenthiazinen
AT340943B (de)	1978-01-10	Verfahren zur herstellung von neuen 1,8-naphthyridin-derivaten
DE2110066A1 (en)	1971-09-23	1-Alkyl-7-alkyl-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids - having bacterial inhibiting effects