1-amino-2-chloro-4-hydroxyanthracene-9,10-dione

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: One part by weight of 1-amino-2-chloro-4-hydroxyanthraquinone, 10 parts by weight of 1,3-dimethyl-2-imidazolidinone, 1.0 part by weight of potassium carbonate and 1.0 part by weight of N,N-di-n-butyl-m-aminophenol were mixed at room temperature, and then heated to 140° C. While this temperature was maintained, the reaction was conducted for 3 hours. The reaction mixture was then cooled to room temperature, charged into 90 parts by weight of water, and extracted with toluene. After the solution was separated, toluene was distilled off under reduced pressure, and the residue was purified through silica gel column chromatography to obtain an anthraquinone compound as coloring matter No. 9 (yield 90%) in Table 1. While this temperature was maintained The reaction mixture was then cooled to room temperature extracted with toluene After the solution was separated toluene was distilled off under reduced pressure the residue was purified through silica gel column chromatography

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: One part of 1-amino-2-chloro-4-hydroxyanthraquinone, 10 parts of 1,3-dimethyl-2-imidazolidinone, 1.0 part of potassium carbonate and 2.0 parts of N,N-di-n-octyl-m-aminophenol were mixed at room temperature, and then heated to 150° C. While this temperature was maintained, the reaction was conducted for 5 hours. The reaction mixture was cooled, then charged into 100 parts of water, extracted with toluene and thereafter purified through silica gel column chromatography to obtain an anthraquinone compound as coloring matter No. 1 (yield 90%). While this temperature was maintained The reaction mixture was cooled extracted with toluene purified through silica gel column chromatography

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 47 parts of ethylene glycol, 13.7 parts of 1-amino-4-hydroxy-2-chloroanthraquinone, 24 parts of N-methylpyrrolidone, 1.2 parts of phenol and 6 parts of potassium carbonate are heated for 6 hours at 120°-125°C under nitrogen. After working up, 10.5 parts of 1-amino-2-(2'-hydroxyethoxy)-4-hydroxyanthraquinone are obtained.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 90 parts of 2,2-dimethyl-1,3-hexanediol, 27.3 parts of 1-amino-4-hydroxy-2-chloroanthraquinone, 45 parts of N-methylpyrrolidone, 9.4 parts of phenol and 12 parts of potassium carbonate are heated for 5 hours at 130°C and 8 hours at 140°C under nitrogen. When cold, the mixture is diluted with 140 parts of methanol and filtered. The filtrate is diluted with water. 21 parts of 1-amino-2-(2',2'-dimethyl-3'-hydroxyhexoxy)-4-hydroxyanthraquinone are obtained. filtered The filtrate is diluted with water

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 90 parts of 2,2-dimethyl-1,3-hexanediol, 27.3 parts of 1-amino-4-hydroxy-2-chloroanthraquinone, 45 parts of N-methylpyrrolidone, 9.4 parts of phenol and 12 parts of potassium carbonate are heated for 5 hours at 130°C and 8 hours at 140°C under nitrogen. When cold, the mixture is diluted with 140 parts of methanol and filtered. The filtrate is diluted with water. 21 parts of 1-amino-2-(2',2'-dimethyl-3'-hydroxyhexoxy)-4-hydroxyanthraquinone are obtained. filtered The filtrate is diluted with water

反応条件: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 25 parts of 3-methyl-1,5-pentanediol, 12 parts of N-methylpyrrolidone, 2.6 parts of phenol and 3.3 parts of potassium carbonate is mixed with 8 parts of 1-amino-4-hydroxy-2-chloroanthraquinone at 130°C and stirred for 3 hours at 130°C and 2 hours at 140°C under nitrogen. After working up, 6 parts of 1-amino-2-(5'-hydroxy-3'-methylpentoxy)-4-hydroxyanthraquinone melting at from 134° to 135°C are obtained.

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A stirred reactor is charged with 184 parts of sulfuric acid monohydrate and 4.8 parts (1 equivalent) of paraformaldehyde are added, with stirring, over about 15 minutes. Stirring is continued until a solution is obtained. This solution is then heated to 60°-65° C. and 46.5 parts of 98% 1-amino-2,4-dichloroanthraquinone are added. The reaction mixture is heated for 1 hour to 110° C. and this temperature is maintained for 3 hours. The mixture is cooled to 100° C. and 870 parts of water are added. The resultant suspension is heated to 90°-95° C. and stirred for 2 hours at this temperature, then cooled and filtered. The filter cake is washed with hot water and the product is dried in vacuo at 80°-90° C., affording 43.3 parts (95% yield) of 1-amino-2-chloro-4-hydroxyanthraquinone. Rf =0.29 (eluant: concentrated formic acid, saturated with 1-bromonaphthalene). are added Stirring is obtained This solution is then heated to 60°-65° C. The reaction mixture is heated for 1 hour to 110° C. this temperature is maintained for 3 hours stirred for 2 hours at this temperature cooled filtered The filter cake is washed with hot water the product is dried in vacuo at 80°-90° C.

反応条件: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: One part by weight of 1-amino-2-chloro-4-hydroxyanthraquinone, 10 parts by weight of 1,3-dimethyl-2-imidazolidinone, 1.0 part by weight of potassium carbonate and 1.0 part by weight of N,N-di-n-butyl-m-aminophenol were mixed at room temperature, and then heated to 140° C. While this temperature was maintained, the reaction was conducted for 3 hours. The reaction mixture was then cooled to room temperature, charged into 90 parts by weight of water, and extracted with toluene. After the solution was separated, toluene was distilled off under reduced pressure, and the residue was purified through silica gel column chromatography to obtain an anthraquinone compound as coloring matter No. 9 (yield 90%) in Table 1. While this temperature was maintained The reaction mixture was then cooled to room temperature extracted with toluene After the solution was separated toluene was distilled off under reduced pressure the residue was purified through silica gel column chromatography

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: One part of 1-amino-2-chloro-4-hydroxyanthraquinone, 10 parts of 1,3-dimethyl-2-imidazolidinone, 1.0 part of potassium carbonate and 2.0 parts of N,N-di-n-octyl-m-aminophenol were mixed at room temperature, and then heated to 150° C. While this temperature was maintained, the reaction was conducted for 5 hours. The reaction mixture was cooled, then charged into 100 parts of water, extracted with toluene and thereafter purified through silica gel column chromatography to obtain an anthraquinone compound as coloring matter No. 1 (yield 90%). While this temperature was maintained The reaction mixture was cooled extracted with toluene purified through silica gel column chromatography

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: One part of 1-amino-2-chloro-4-hydroxyanthraquinone, 10 parts of 1,3-dimethyl-2-imidazolidinone, 1.0 part of potassium carbonate and 2.0 parts of N,N-di-n-octyl-m-aminophenol were mixed at room temperature, and then heated to 150° C. While this temperature was maintained, the reaction was conducted for 5 hours. The reaction mixture was cooled, then charged into 100 parts of water, extracted with toluene and thereafter purified through silica gel column chromatography to obtain an anthraquinone compound as coloring matter No. 1 (yield 90%). While this temperature was maintained The reaction mixture was cooled extracted with toluene purified through silica gel column chromatography

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 29.75 g of 1-amino-2-chloro-4-hydroxyanthraquinone (titer 92%), 120 ml of chlorobenzene, 5 g of tetrabutylammonium bromide, 10.8 g of phenol and 6.48 g of potassium hydroxide are heated within 1 hour, with stirring, to boiling temperature (131°-133° C.), and then stirred for 5 hours at the boiling temperature. Reaction water occurring during the process is distilled off at the side, together with about 10 ml of chlorobenzene. The reaction mixture is subsequently cooled to 60° C., and 50 ml of methanol are added; the precipitate is filtered off, washed with methanol and water and then dried. The yield is 29.9 g of 1-amino-4-hydroxy-2-phenoxyanthraquinone (90.3% of theory). The product dyes polyester in exactly the same manner as the commercial product does, produced from 1-amino-2-chloro-4-hydroxyanthraquinone in phenol in the presence of phenolate. temperature (131°-133° C.) stirred for 5 hours at the boiling temperature is distilled off at the side, together with about 10 ml of chlorobenzene 50 ml of methanol are added the precipitate is filtered off washed with methanol and water dried