GB730088A - Substituted indolines and a process for the reduction of naphthostyrils - Google Patents

Substituted indolines and a process for the reduction of naphthostyrils

Info

Publication number
GB730088A
GB730088A GB24900/51A GB2490051A GB730088A GB 730088 A GB730088 A GB 730088A GB 24900/51 A GB24900/51 A GB 24900/51A GB 2490051 A GB2490051 A GB 2490051A GB 730088 A GB730088 A GB 730088A
Authority
GB
United Kingdom
Prior art keywords
ether
benz
naphthostyril
indoline
compounds
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
GB24900/51A
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.)
Sandoz AG
Original Assignee
Sandoz 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
Application filed by Sandoz AG filed Critical Sandoz AG
Publication of GB730088A publication Critical patent/GB730088A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Abstract

The invention comprises benz (cd) indoline of the formula <FORM:0730088/IV (b)/1> and derivatives thereof in which the nucleus A is substituted or has a further cyclic structure fused on it. The above compounds are prepared by a process characterized in that naphthostyril having the formula <FORM:0730088/IV (b)/2> or a derivative thereof in which the nucleus B is substituted or has a further cyclic structure fused on it is treated with a reducing agent selected from the group consisting of metal hydrides. Solvents which may be employed are ethylmorpholine, tetrahydrofurane, ether and dioxane. Lithium aluminium hydride is specified as reducing agent and room or slightly elevated temperature may be used. The benz (cd) indolines oxidize rapidly in air, especially in an acid medium. Stable acetyl derivatives may be obtained by treatment of the benz (cd) indolines with acetic anhydride in pyridine. In examples: benz (cd) indoline is obtained by adding lithium aluminium hydride to naphthostyril in ethylmorpholine at elevated temperature, hydrolysing the reacted mixture with water, shaking with ether and caustic soda lye and drying and evaporating the ether solution (1); 4-piperidyl (11) (cd) indoline is similarly obtained from 4-piperidyl (11) naphthostyril (2); compounds of the formul <FORM:0730088/IV (b)/3> and <FORM:0730088/IV (b)/4> are similarly obtained from the compounds of formul <FORM:0730088/IV (b)/5> and <FORM:0730088/IV (b)/6> respectively, the products being crystallized from petroleum ether (1) or ethyl acetate (3) or distilled under reduced pressure (2) and acetyl derivatives being recrystallized from ether (1, 2), alcohol (3) or a mixture of methylene chloride and alcohol (4). Specifications 670,991 705,436 and 728,660 are referred to.
GB24900/51A 1950-10-26 1951-10-24 Substituted indolines and a process for the reduction of naphthostyrils Expired GB730088A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH730088X 1950-10-26

Publications (1)

Publication Number Publication Date
GB730088A true GB730088A (en) 1955-05-18

Family

ID=4532288

Family Applications (1)

Application Number Title Priority Date Filing Date
GB24900/51A Expired GB730088A (en) 1950-10-26 1951-10-24 Substituted indolines and a process for the reduction of naphthostyrils

Country Status (1)

Country Link
GB (1) GB730088A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3081513A (en) * 1959-02-19 1963-03-19 Schweizerische Viscose Process for the production of wash-and-wear characteristics in woven fabrics of regenerated cellulose
US3673182A (en) * 1967-09-04 1972-06-27 Bayer Ag Naphtholactam-(1,8) basic dyestuffs

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3081513A (en) * 1959-02-19 1963-03-19 Schweizerische Viscose Process for the production of wash-and-wear characteristics in woven fabrics of regenerated cellulose
US3673182A (en) * 1967-09-04 1972-06-27 Bayer Ag Naphtholactam-(1,8) basic dyestuffs

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