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US4014906A
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Process for the manufacture of anthraquinone compounds
Assignee: Novartis Corp
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Filing: 1975-12-10
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Granted: 1977-03-29
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Expires: 1995-12-10
Abstract
Abstract A process for the manufacture of anthraquinone compounds of formula ##STR1## wherein X represents a hydrogen atom or a substituted or unsubstituted lower alkyl radical of 1 to 6 carbon atoms or a substituted or unsubstituted aryl radical, and the ring A can be further substituted, by sulphonating 1,5-dialkoxy-, 1,5-dicycloalkoxy- or diaryloxy-anthraquinone in the 2 and 6 positions, introducing two amino groups in positions 4 and 8 by treating the sulphonated intermediate with hydroxylamine or a salt thereof in sulphuric acid medium, in the presence of a metal catalyst, introducing the radical ##STR2## by reacting the boric acid complex of 1,5-dihydroxy-4,8-diaminoanthraquinone-2,6-disulphonic acid with a compound of formula ##STR3## saponifying the boric acid groups and splitting off a SO 3 H group, which process comprises using 1,5-dialkoxy-, 1,5-dicycloalkoxy- or 1,5-diaryloxyanthraquinone as starting compounds and reacting them to give the end product of formula I.
Inventors
- 👤 Urs Karlen
- 👤 Hans Morawietz
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 02:14
CPC Classifications
C; C09; C09B; C09B1/00; C09B1/50; C09B1/52; C09B1/521
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
143 words
A process for the manufacture of anthraquinone compounds of formula ##STR8## wherein X represents a hydrogen atom or a substituted or unsubstituted lower alkyl radical of 1 to 6 carbon atoms or a substituted or unsubstituted aryl radical, and the ring A can be further substituted, by sulphonating 1,5-dialkoxy-, 1,5-dicycloalkoxy- or diaryloxy-anthraquinone in the 2 and 6 positions, introducing two amino groups in positions 4 and 8 by treating the sulphonated intermediate with hydroxylamine or a salt thereof in sulphuric acid medium, in the presence of a metal catalyst, introducing the radical ##STR9## by reacting the boric acid complex of 1,5-dihydroxy-4,8-diaminoanthraquinone-2,6-disulphonic acid with a compound of formula ##STR10## saponifying the boric acid groups and splitting off a SO 3 H group, which process comprises using 1,5-dialkoxy-, 1,5-dicycloalkoxy- or 1,5-diaryloxyanthraquinone as starting compounds and reacting them to give the end product of formula I.
Claim 2
Dependent Claim
143 words
A process for the manufacture of anthraquinone compounds of formula ##STR8## wherein X represents a hydrogen atom or a substituted or unsubstituted lower alkyl radical of 1 to 6 carbon atoms or a substituted or unsubstituted aryl radical, and the ring A can be further substituted, by sulphonating 1,5-dialkoxy-, 1,5-dicycloalkoxy- or diaryloxy-anthraquinone in the 2 and 6 positions, introducing two amino groups in positions 4 and 8 by treating the sulphonated intermediate with hydroxylamine or a salt thereof in sulphuric acid medium, in the presence of a metal catalyst, introducing the radical ##STR9## by reacting the boric acid complex of 1,5-dihydroxy-4,8-diaminoanthraquinone-2,6-disulphonic acid with a compound of formula ##STR10## saponifying the boric acid groups and splitting off a SO 3 H group, which process comprises using 1,5-dialkoxy-, 1,5-dicycloalkoxy- or 1,5-diaryloxyanthraquinone as starting compounds and reacting them to give the end product of formula I.
Claim 3
Dependent Claim
23 words
A process according to claim 1 which comprises the use of a vanadium catalyst as metal catalyst and hydroxylamine sulphate as hydroxylamine salt.
Claim 4
Dependent Claim
43 words
A process according to claim 1, wherein mono-, di- or trialkoxybenzene, mono-, di- or trihydroxybenzene, monohydroxymonoalkoxybenzene, monohydroxymonoalkylbenzene, monohydroxymonophenylbenzene, monohydroxydialkylbenzene, monoalkoxymonoalkylbenzene, monoalkoxymonoalkenylbenzene, monohydroxymonoalkoxymonoalkylbenzene, ω-haloalkoxybenzene, 1-hydroxy-2- or -3-halobenzene, (2'-hydroxyethoxy)-benzene or a benzene with a fused oxygen-containing heterocyclic ring, is used as compound of formula II.
Claim 5
Dependent Claim
23 words
A process according to claim 3 which comprises the use of phenol, methoxyphenol, ethoxybenzene, ω-hydroxyethoxybenzene or a cresol as compounds of formula II.
Claim 6
Dependent Claim
27 words
A process according to claim 1, wherein the boric acid complex of 1,5-dihydroxy-4,8-diaminoanthraquinone-2,6-disulphonic acid is reacted with a mixture of compounds that contain alkoxy and/or hydroxyphenyl groups.
Claim 7
Dependent Claim
25 words
A process according to claim 5 which comprises the use of a mixture of phenol with methoxybenzene in the weight ratio of 1:5 to 5:1.
Claim 8
Dependent Claim
22 words
A process according to claim 1, wherein the 1,5-dialkoxy-, 1,5-dicycloalkoxy- or 1,5-diaryloxy-anthraquinone is obtained by substitution of 1,5-dinitroanthraquinone with alcoholates or phenolates.
Claim 9
Dependent Claim
16 words
A process according to claim 7, wherein 1,5-dimethoxy-, 1,5-diethoxy- or 1,5-diisopropoxy-anthraquinone is used as starting product.
Claim 10
Dependent Claim
46 words
A process for the manufacture of anthraquinone compounds, wherein the 1,5-dinitroanthraquinone used as starting product is reacted with alcoholates or hydroxyarylates to give the corresponding 1,5-dialkoxy, 1,5-dicycloalkoxy or 1,5-diaryloxy compounds and these are further reacted according to claim 1 to give anthraquinone compounds of formula I.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-03-28 | 1980-09-27 | 1981-03-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-03-28 | 1984-09-27 | 1985-03-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-03-28 | 1988-09-27 | 1989-03-29 | $7700.00 | Window Closed / Lapsed |