DD218617A1 - Verfahren zur herstellung von oh-substituierten chinolinen - Google Patents

Verfahren zur herstellung von oh-substituierten chinolinen Download PDF

Info

Publication number: DD218617A1
Authority: DD; German Democratic Republic
Prior art keywords: preparation; methyl; substituted; acetylacetone; chinolines
Prior art date: 1983-07-01

Application number

DD25263583A

Other languages

German (de)

English (en)

Inventor

Bodo Hirsch

Milan Adamek

Viktor Milakow

Original Assignee

Univ Dresden Tech

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.)

1983-07-01

Filing date

1983-07-01

Publication date

1985-02-13

1983-07-01 Application filed by Univ Dresden Tech filed Critical Univ Dresden Tech

1983-07-01 Priority to DD25263583A priority Critical patent/DD218617A1/de

1983-11-01 Priority to CS838057A priority patent/CS240772B1/cs

1985-02-13 Publication of DD218617A1 publication Critical patent/DD218617A1/de

Links

238000004519 manufacturing process Methods 0.000 title 1
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims abstract description 10
CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 claims abstract description 9
238000000034 method Methods 0.000 claims abstract description 9
238000002360 preparation method Methods 0.000 claims abstract description 9
238000006243 chemical reaction Methods 0.000 claims abstract description 6
CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 claims abstract description 5
229940018563 3-aminophenol Drugs 0.000 claims abstract description 5
239000003960 organic solvent Substances 0.000 claims abstract description 3
239000011541 reaction mixture Substances 0.000 claims abstract description 3
229940111121 antirheumatic drug quinolines Drugs 0.000 claims description 4
150000003248 quinolines Chemical class 0.000 claims description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims 1
239000012024 dehydrating agents‎ Substances 0.000 claims 1
239000000203 mixture Substances 0.000 claims 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 6
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 6
FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical class C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000013078 crystal Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 2
239000002585 base Substances 0.000 description 2
239000012458 free base Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000000243 solution Substances 0.000 description 2
239000007858 starting material Substances 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
BJMQFQNRVVIERR-UHFFFAOYSA-N 2,4-dimethylquinolin-7-ol Chemical compound C1=CC(O)=CC2=NC(C)=CC(C)=C21 BJMQFQNRVVIERR-UHFFFAOYSA-N 0.000 description 1
UZSDRHVOBLQYCX-UHFFFAOYSA-N 2-amino-6-hydroxybenzoic acid Chemical compound NC1=CC=CC(O)=C1C(O)=O UZSDRHVOBLQYCX-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
UNPLRYRWJLTVAE-UHFFFAOYSA-N Cloperastine hydrochloride Chemical compound Cl.C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)OCCN1CCCCC1 UNPLRYRWJLTVAE-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
125000005210 alkyl ammonium group Chemical group 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD25263583A 1983-07-01 1983-07-01 Verfahren zur herstellung von oh-substituierten chinolinen DD218617A1 (de)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
DD25263583A DD218617A1 (de)	1983-07-01	1983-07-01	Verfahren zur herstellung von oh-substituierten chinolinen
CS838057A CS240772B1 (en)	1983-07-01	1983-11-01	Method of 7-hydroxyquinoline derivatives production

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DD25263583A DD218617A1 (de)	1983-07-01	1983-07-01	Verfahren zur herstellung von oh-substituierten chinolinen

Publications (1)

Publication Number	Publication Date
DD218617A1 true DD218617A1 (de)	1985-02-13

Family

ID=5548717

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD25263583A DD218617A1 (de)	1983-07-01	1983-07-01	Verfahren zur herstellung von oh-substituierten chinolinen

Country Status (2)

Country	Link
CS (1)	CS240772B1 (cs)
DD (1)	DD218617A1 (cs)

1983
- 1983-07-01 DD DD25263583A patent/DD218617A1/de not_active IP Right Cessation
- 1983-11-01 CS CS838057A patent/CS240772B1/cs unknown

Also Published As

Publication number	Publication date
CS240772B1 (en)	1986-02-13
CS805783A1 (en)	1985-07-16

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1995-03-16	ENJ	Ceased due to non-payment of renewal fee