GB508708A - Improvements in the manufacture and production of anthraquinone derivatives - Google Patents

Abstract

508,708. Dyes. JOHNSON, G. W. (I. G. Farbenindustrie Akt.-Ges.) Jan. 14, 1938, No. 1348. [Class 2 (iii)] 1.2-Pyridino- and 1.2-pyridono-anthraquinones and anthraquinone-acridines . are made' by 'reacting aminoanthraquinone-o-aldehydes in sulphuric or phosphoric acid with ketones containing a methylene group adjacent to the carbonyl group, with free or esterified malonic or cyanacetic acid or with one of the following: resorcinol, phloroglucinol, and alpha- or #-naphthol, 2.6- and 2.7-dihydroxynaphthalene, aminohydroxynaphthalenes, hydroxynaphthalene carboxylic acids and sulphonic acids, hydroxy anthracenes, hydroxyphenanthrenes, hydroxyazaphenanthrenes, hydroxythionaphthenes. Ketones specified are acetone, methyl ethyl ketone, acetyl acetone, acetophenone and its derivatives substituted in the aryl radical, methyl naphthyl ketones, desoxybenzoin, acetylanthracenes, acetylphenanthrenes cyclohexanonebarbituric acid, 2.5-diketopipÚrazines, hydantoines, naphthindandiones and naphthalene di-indandiones. In examples : (i.) l.aminoanthraquinone-2-aldehyde is reacted in concentrated sulphuric acid with #-naphthol to give anthraquinone- 1(N).2.2<1>(N). 1<1>-naphthacridine, which may be oxidized with chromic acid to give a substance dyeing cotton red shades; alpha-naphthol may replace the #-naphthol, and 2:6- or 2.7-dihydroxynaphthalene may react with one or two molecular proportions of 1-aminoanthraquinone-2-aldehyde ; 2-aminoanthraquinone-3-aldehyde may be reacted with #-naphthol; ,(2) 1-aminoanthraquinone-2-aldehyde is reacted with 2-hydroxynaphthalene-3 (or 5 or 6)-carboxylic acid to give anthraquinone-1(N).2.2<1>(N).1<1>-naphthacridine-31 (or 51 or 6<1>)-carboxylic acid ; (3) 1- aminoanthraquinone-2-aldehyde is reacted with 2-amino-7-naphthol in sulphuric acid to give anthraquinone-1(N).2.2<1>(N).1<1>. 7<1>-aminonaphthacridine; 1 amino-7-naphthol or 1-amino-3- naphthol may also be used; (4) 1 aminoanthraquinone-2-aldehyde is reacted with 2- hydroxyanthracene to give anthraquinone- 1(N)2.2<1>(N).1<1>-anthracene acridine, which maybe oxidized with chromic acid to give a yellowred dyestuff for cotton ; (5) 1-aminoanthraquinone.-2-aldehyde is reacted with #-naphthol in phosphoric acid to give the same product as in (1) ; (6) I-aminoanthraquinone-2-aldehyde is reacted with .barbituric acid to give anthraquinone-1(N).2.2<1>(N).1<1>-3<1>.5<1>-diaza-4<1>.6<1> dihydroxybenzacridine, which may be converted to, a dichlor derivative by reaction with phosphorus pentachloride; the barbituric acid may be replaced by 2.5-diketopiperazine, hydantoin or 1-phenylhydantoin (7) phloroglucinol is reacted with one, two, or three molecular proportions of 1-aminoanthraquinone- 2-aldehyde to give violet dyes for cotton; resorcinol may also be used; (8) 1-aminoanthraquinone-2-adehyde is reacted with perinaphthindandione or naphthalene-1.8.4.5-diindandione; (9) 1-aminoanthraquinone-2-aldehyde is reacted with acetophenone to give Py. 2-phenyl-1(N)-2-pyridinoanthraquinone ; the acetophenone may be replaced by p-amino-, p-methoxy-, p-methyl-, or m-nitro-acetophenone; (10) 1-aminoanthraquinone-2-aldehyde is reacted with 2- or 1-acetylnaphthatene to give Py.2-naphthyl-(2<1> or 1<1>)-1(N).2-pyridinoanthraquinone; (11) 1-aminoanthraquinone- 2,-aldehyde is reacted with 2-acetylanthracene to give Py.2-anthracyl-(2<1>)-1(N).2-pyridnoanthraquinone, which may be oxidized with chromic acid to give Py.2-anthraquinonyl- (2<1>)-1(N).2-pyridinoanthraquinone ; (12) 1- aminoanthraquinone-2-aldehyde is reacted with malonic acid or its esters to give anthraquinone- 1(N).2-pyridono-Py.3-carboxylic acid or with cyanacetic acid or its esters to give an anthraquinone-1(N).2-pyridono derivative.