NO130727B - - Google Patents
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- Publication number
- NO130727B NO130727B NO00462/70A NO46270A NO130727B NO 130727 B NO130727 B NO 130727B NO 00462/70 A NO00462/70 A NO 00462/70A NO 46270 A NO46270 A NO 46270A NO 130727 B NO130727 B NO 130727B
- Authority
- NO
- Norway
- Prior art keywords
- group
- nitro
- stands
- general formula
- hydroxy
- Prior art date
Links
- RPJWQGVDVSVGPQ-UHFFFAOYSA-N 7-nitroquinolin-8-ol Chemical class C1=CN=C2C(O)=C([N+]([O-])=O)C=CC2=C1 RPJWQGVDVSVGPQ-UHFFFAOYSA-N 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- -1 nitro- Chemical class 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- QSIZKIGPOVCSFN-UHFFFAOYSA-N 8-hydroxy-7-nitroquinoline-5-sulfonic acid Chemical compound C1=CN=C2C(O)=C([N+]([O-])=O)C=C(S(O)(=O)=O)C2=C1 QSIZKIGPOVCSFN-UHFFFAOYSA-N 0.000 description 3
- LGDFHDKSYGVKDC-UHFFFAOYSA-N 8-hydroxyquinoline-5-sulfonic acid Chemical compound C1=CN=C2C(O)=CC=C(S(O)(=O)=O)C2=C1 LGDFHDKSYGVKDC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 238000006396 nitration reaction Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- FOIRQVGKEYALLW-UHFFFAOYSA-N (7-nitroquinolin-8-yl) acetate Chemical compound [N+](=O)([O-])C1=CC=C2C=CC=NC2=C1OC(C)=O FOIRQVGKEYALLW-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003248 quinolines Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
- YPEUTQKEMPFPKO-UHFFFAOYSA-N 5,7-dinitroquinolin-8-ol Chemical compound C1=CN=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 YPEUTQKEMPFPKO-UHFFFAOYSA-N 0.000 description 1
- VFTOHJFKIJLYKN-UHFFFAOYSA-N 7-nitro-9h-fluoren-2-ol Chemical group [O-][N+](=O)C1=CC=C2C3=CC=C(O)C=C3CC2=C1 VFTOHJFKIJLYKN-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000002560 therapeutic procedure 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
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
- C07D215/32—Esters
-
- 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
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
- C07D215/28—Alcohols; Ethers thereof with halogen atoms or nitro radicals in positions 5, 6 or 7
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1267669 | 1969-02-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO130727B true NO130727B (nl) | 1974-10-21 |
| NO130727C NO130727C (nl) | 1975-01-29 |
Family
ID=11142657
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO462/70A NO130727C (nl) | 1969-02-10 | 1970-02-10 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3793314A (nl) |
| AT (1) | AT298489B (nl) |
| BE (1) | BE745258A (nl) |
| CH (1) | CH511229A (nl) |
| DE (1) | DE2005959C3 (nl) |
| ES (1) | ES376391A1 (nl) |
| FI (1) | FI49032C (nl) |
| FR (1) | FR2034532B1 (nl) |
| GB (1) | GB1299753A (nl) |
| IL (1) | IL33560A (nl) |
| NL (1) | NL7000974A (nl) |
| NO (1) | NO130727C (nl) |
| SE (1) | SE349803B (nl) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH528214A (de) * | 1970-02-13 | 1972-09-30 | Ciba Geigy Ag | Schädlingsbekämpfungsmittel |
| US3984417A (en) * | 1971-12-27 | 1976-10-05 | Ajinomoto Co., Inc. | Method of producing active amino acid esters |
| US4168311A (en) * | 1973-12-10 | 1979-09-18 | Hoechst Aktiengesellschaft | Hydroxyquinoline carbamates and n-oxide hydroxyquinoline carbamates and their use as insecticides |
| CH732174A4 (nl) * | 1974-05-29 | 1975-10-31 | ||
| US3997542A (en) * | 1975-06-23 | 1976-12-14 | Sterling Drug Inc. | 1-(Halogenated-acetyl)-1,2,3,4-tetrahydro-6-quinolinols and esters thereof |
| DE3621540A1 (de) * | 1986-06-27 | 1988-01-07 | Basf Ag | Chinolinderivate, verfahren zu ihrer herstellung, diese enthaltende mikrobizide und ihre verwendung zur bekaempfung von bakterien und pilzen |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1148405A (en) * | 1966-08-18 | 1969-04-10 | Produits Chemiques Soc Et | Esters derived from nitroquinoline |
-
1969
- 1969-12-18 IL IL6933560A patent/IL33560A/xx unknown
-
1970
- 1970-01-19 US US00004065A patent/US3793314A/en not_active Expired - Lifetime
- 1970-01-23 NL NL7000974A patent/NL7000974A/xx unknown
- 1970-01-28 GB GB4092/70A patent/GB1299753A/en not_active Expired
- 1970-01-30 BE BE745258D patent/BE745258A/xx unknown
- 1970-02-03 FI FI700296A patent/FI49032C/fi active
- 1970-02-06 FR FR707004270A patent/FR2034532B1/fr not_active Expired
- 1970-02-09 ES ES376391A patent/ES376391A1/es not_active Expired
- 1970-02-09 AT AT116270A patent/AT298489B/de not_active IP Right Cessation
- 1970-02-09 SE SE01589/70A patent/SE349803B/xx unknown
- 1970-02-10 CH CH190970A patent/CH511229A/fr not_active IP Right Cessation
- 1970-02-10 NO NO462/70A patent/NO130727C/no unknown
- 1970-02-10 DE DE2005959A patent/DE2005959C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FI49032C (fi) | 1975-03-10 |
| GB1299753A (en) | 1972-12-13 |
| CH511229A (fr) | 1971-08-15 |
| DE2005959C3 (de) | 1973-10-11 |
| US3793314A (en) | 1974-02-19 |
| BE745258A (fr) | 1970-07-01 |
| NL7000974A (nl) | 1970-08-12 |
| AT298489B (de) | 1972-05-10 |
| DE2005959B2 (de) | 1973-03-15 |
| FR2034532A1 (nl) | 1970-12-11 |
| FI49032B (nl) | 1974-12-02 |
| SE349803B (nl) | 1972-10-09 |
| IL33560A0 (en) | 1970-02-19 |
| IL33560A (en) | 1973-04-30 |
| ES376391A1 (es) | 1972-04-01 |
| DE2005959A1 (de) | 1970-08-06 |
| NO130727C (nl) | 1975-01-29 |
| FR2034532B1 (nl) | 1973-08-10 |
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