GB1380833A - Process for the production of substituted benzo-c-cinnolines - Google Patents

Process for the production of substituted benzo-c-cinnolines

Info

Publication number
GB1380833A
GB1380833A GB1722372A GB1722372A GB1380833A GB 1380833 A GB1380833 A GB 1380833A GB 1722372 A GB1722372 A GB 1722372A GB 1722372 A GB1722372 A GB 1722372A GB 1380833 A GB1380833 A GB 1380833A
Authority
GB
United Kingdom
Prior art keywords
benzo
nitrobenzene
hydroxy
solvent
sulpho
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
Application number
GB1722372A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer 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.)
Filing date
Publication date
Priority claimed from DE19712118491 external-priority patent/DE2118491B2/en
Priority claimed from DE19722203461 external-priority patent/DE2203461C3/en
Application filed by Bayer AG filed Critical Bayer AG
Publication of GB1380833A publication Critical patent/GB1380833A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
    • C07D237/36—Benzo-cinnolines

Abstract

1380833 Benzo-(c)-cinnoline derivatives and their preparation BAYER AG 14 April 1972 [16 April 1971 26 Jan 1972] 17223/72 Heading C2C Benzo-(c)-cinnoline derivatives of the formula wherein R<SP>1</SP>, R<SP>2</SP>, R<SP>3</SP> and R<SP>4</SP> are the same or different and each represents a hydrogen or halogen atom, or an alkyl radical having from 1 to 8 carbon atoms, and n is 0 or 1, may be obtained by reacting a 2-nitrobenzene-sulpho- 3<SP>1</SP>-hydroxy anilide of the formula with at least two acid equivalents of an alkaline reagent at a temperature of 20-400‹ C. and working the product up by a known method. The reaction may be carried out in water or an organic solvent, optionally under elevated pressure, and the alkaline reagent may be, for example, an. oxide, hydroxide or weak acid salt of an alkali or alkaline earth metal or a quaternary ammonium base, or an alcoholate of a C 1-5 alcohol with an alkali or alkaline earth metal. Reaction temperatures of 200-400‹ C. and the use of water as solvent favours the formation of the benzo-(c)-cinnoline derivative, whilst reaction temperatures of 20-150‹ C. and the use of dimethyl sulphoxide as solvent favours the formation of the corresponding N-oxides. 2 - Nitrobenzene sulpho - 3<SP>1</SP> - hydroxy - 4<SP>1</SP>- methyl anilide is obtained by reacting 4-amino- 2-hydroxy toluene with 2-nitrobenzene sulphochloride at pH 4 or 5.
GB1722372A 1971-04-16 1972-04-14 Process for the production of substituted benzo-c-cinnolines Expired GB1380833A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19712118491 DE2118491B2 (en) 1971-04-16 1971-04-16 PROCESS FOR THE MANUFACTURING OF 3-HYDROXY-BENZO SQUARE CLAMP ON CINNOLINE DERIVATIVES
DE19722203461 DE2203461C3 (en) 1972-01-26 1972-01-26 Process for the preparation of halogen-substituted 3-hydroxybenzo [c] -cinnoline derivatives

Publications (1)

Publication Number Publication Date
GB1380833A true GB1380833A (en) 1975-01-15

Family

ID=25760975

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1722372A Expired GB1380833A (en) 1971-04-16 1972-04-14 Process for the production of substituted benzo-c-cinnolines

Country Status (5)

Country Link
JP (1) JPS5234632B1 (en)
CH (1) CH563371A5 (en)
FR (1) FR2136444A5 (en)
GB (1) GB1380833A (en)
IT (1) IT961102B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH644459A5 (en) 1978-09-29 1984-07-31 Ciba Geigy Ag METHOD FOR PRODUCING COLOR PHOTOGRAPHIC IMAGES AFTER THE SILVER COLORING METHOD.

Also Published As

Publication number Publication date
JPS5234632B1 (en) 1977-09-05
CH563371A5 (en) 1975-06-30
IT961102B (en) 1973-12-10
FR2136444A5 (en) 1972-12-22

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee