GB377419A - Process for the preparation of new condensation products of the anthraquinone series - Google Patents

Process for the preparation of new condensation products of the anthraquinone series

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Publication number
GB377419A
GB377419A GB20544/31A GB2054431A GB377419A GB 377419 A GB377419 A GB 377419A GB 20544/31 A GB20544/31 A GB 20544/31A GB 2054431 A GB2054431 A GB 2054431A GB 377419 A GB377419 A GB 377419A
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GB
United Kingdom
Prior art keywords
amino
condensed
give
ester
methyl
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
GB20544/31A
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 GB377419A publication Critical patent/GB377419A/en
Expired legal-status Critical Current

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Abstract

Anthrapyridones are prepared by condensing anthraquinone derivatives of the general formula: <FORM:0377419/IV/1> wherein R represents hydrogen or an alkyl group, X represents hydrogen, a halogen, or an alkyl or alkoxy group, Y represents hydrogena halogen, or a hydroxy, alkoxy, amino, alkylamino or arylamino group, Z represents hydro, gen, a halogen, or a hydroxy, alkoxy, amino, alkylamino or arylamino group, with esters of the formula: RCOCH2COO alkyl, wherein R represents an alkyl, alkoxy, or phenyl group, in the presence of condensing agents of a weak basic character and in the presence or absence of organic solvents. The products are C-carbalkoxy-or-C-acetylanthrapyridones according to the ester employed in the condensation. The presence of a condensing agent is essential if the starting materials are pure, but with commercial initial materials they may be dispensed with. Suitable weakly basic condensing agents are formates, acetates, nitrites, carbonates, borates, sulphites of alkali metals, calcium oxide, magnesium oxide. In examples a -aminoanthraquinone is condensed with diethylmalonate in presence of sodium acetate to give C-carbethoxyanthrapyridone; 1 : 5-diaminoanthraquinone is condensed with acetoacetic ester in presence of sodium acetate to give a C : C<1>-diacetylanthrapyridone; 1-methyl-amino-4-bromanthraquinone is condensed with ethyl malonate in presence of sodium acetate and with acetoacetic ester to C-carbethoxy- and C-acetyl-N-methyl-4-bromanthrapyridone; 1-methylamino-5-chloranthraquinone is condensed with acetoacetic ester in presence of sodium carbonate or sodium or potassium acetate to give 5-chlor-C-acetyl-N-methylanthrapyridone; 1-amino-2-methyl-4-bromanthraquinone is condensed with malonic ester or acetoacetic ester in presence of sodium carbonate (or calcium oxide), magnesium oxide, sodium phosphate or sodium sulphite to give 2-methyl-4-bromo-C-carbethoxy- and C-acetylanthrapyridone; 1-amino-2 : 4-dibromanthraquinone is condensed with malonic ester or acetoacetic ester to give C-carbethoxy or C-acetyl-2 : 4-dibromanthrapyridone; 1-amino-4-methoxyanthraquinone is condensed with acetoacetic ester in presence of sodium acetate or with malonic ester to give C-acetyl- or C-carbethoxy-4-methoxyanthrapyridone, 1-amino-5-oxyanthraquinone is condensed with malonic ester or acetoacetic ester to give C-carbethoxy-or-C-acetyl-5-oxyanthrapyridone; 1-amino-2-bromo-4-p-toluidoanthraquinone is condensed with malonic ester or acetoacetic ester to give 4-p-toluido-2-bromo-C-carbethoxy-pyridone or 4-p-toluido-2-bromo-C-acetylanthra-pyridone; instead of 1-amino-2-brom-4-p-toluidoanthraquinone other arylaminoanthraquinones may be used such as the anilido-, xylidino, chloranilido, amidophenolethers-, amidocresolethers, phenylenediamido derivatives, or 1-amino-2-methyl-4-arylaminoanthraquinones, 1-amino-4-arylaminoanthraquinones-1-amino-5-arylaminoanthraquinone may be, employed: 1-amino-2-methyl-4-bromanthraquinone is condensed with benzoylacetic ester in presence of sodium acetate to give C-benzoyl-2-methyl-4-bromanthrapyridone. It is also stated that 1-aminoanthraquinone may be condensed with malonic ester to give o -carbethoxyacetylaminoanthraquinone which is converted on boiling with an aqueous caustic soda solution into a C-carboxyanthrapyridone. Specifications 28765/06, [Class 2, Acids and salts, Organic &c.], and 299,349, [Class 2 (iii), Dyes &c.], are referred to.
GB20544/31A 1930-07-18 1931-07-17 Process for the preparation of new condensation products of the anthraquinone series Expired GB377419A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE377419X 1930-07-18

Publications (1)

Publication Number Publication Date
GB377419A true GB377419A (en) 1932-07-28

Family

ID=6344393

Family Applications (1)

Application Number Title Priority Date Filing Date
GB20544/31A Expired GB377419A (en) 1930-07-18 1931-07-17 Process for the preparation of new condensation products of the anthraquinone series

Country Status (1)

Country Link
GB (1) GB377419A (en)

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