1, 5-dihydroxy-8-nitro-4-aminoanthraquinone compounds

m-Aminophenylethyl alcohol is made by hydrogenation of m-nitrophenylacetic acid to m-aminophenylacetic acid, which is reduced with lithium aluminium hydride in ether. o- and p-1,3-Dihydroxypropylaniline are obtained by nitrating the diacetate of 3-phenyl-1,3-propanediol, separating by ether extraction the 3-(o-nitrophenyl)-1,3-propanediol diacetate from the 3-(p-nitrophenyl)-1,3-propanediol diacetate, and reducing and hydrolysing each. 3 - Amino - 4 - methoxybenzyl alcohol is obtained by hydrogenation of 4-methoxy-3-nitrobenzaldehyde. 3 - Chloro - 4 - aminophenylmethyl carbinol is obtained by ammonolysis followed by hydrogenation of 3,4-dichloroacetophenone. 4 - Methyl - 3 - aminophenylmethylcarbinol is obtained by nitration, followed by hydrogenation, from p-methylacetophenone. m-Aminophenylethylcarbinol is obtained from propiophenone by nitration, followed by hydrogenation. 1,5-Dihydroxy-4-chloro- or bromo-8-fluoranthraquinone is prepared by chlorinating or brominating 1,5 - dihydroxy - 8 - fluoranthraquinone.ALSO:The invention includes dyes of the formula: wherein X is a monohydroxyalkyl group of 1-3 carbon atoms or a dihydroxalkyl group of 2-3 carbon atoms, Y is hydrogen, chlorine, hydroxy, methoxy, or methyl, and Z is fluorine, chlorine, or bromine. They are made by condensing a compound of the formula: where Q is chlorine or bromine, with a primary arylamine of the formula: Diluents specified for the reaction comprise alcohols, glycols, glycol ethers, fatty acid N.N-dialkylamides, or an excess of the arylamine. The products dye cellulose esters, e.g. the acetate, propionate, butyrate, acetate-propionate, and acetate-butyrate, by applying as a suspension made by grinding in presence of a sulphonated oil, soap, sodium lignin sulphonate, or other dispersing agent. In examples, 1.5-dihydroxy-4.8-dichloranthraquinone is condensed with 91) o- or p-aminophenylethyl alcohol, (2) m-aminobenzyl alcohol, (3) o-, m-, or p-aminophenylmethylcarbinol, (4) o- or p-(1.3-dihydroxypropyl) -aniline, (5) p-(1.2-dihydroxyethyl) aniline, (6) 2-methoxy-, 2-chloro-, or 2-hydroxy-5-b -hydroxyethyl-aniline, (7) 2-methyl-5-a -hydroxyethyl-aniline, (8) 6-amino-3-methylbenzyl alcohol, (9) 3-amino-4-methoxybenzyl alcohol, (10) 3-chloro-4-aminophenylmethylcarbinol, (11) 4-methyl-3-aminophenylmethylcarbinol, (12) m-aminophenylethylcarbinol. Also in examples (13) 1.5-dihydroxy-4-chloro-8-fluoro-anthraquinone is cond