81-39-0

Usage

Uses

Used in Plastics Industry:
Solvent Red 52 is used as a coloring agent for acetate, polyethylene, and other thermal plastic materials. Its vibrant red hue and solubility properties make it a suitable choice for imparting color to these plastics, enhancing their aesthetic appeal and functionality.
Used in Chemical Synthesis:
In the production of Poly(trimethylene furandicarboxylate), a bio-based polymer with potential applications in packaging and textile industries, Solvent Red 52 plays a crucial role. It is utilized in a method that employs a Zinc catalyst, facilitating the synthesis process and contributing to the development of sustainable and eco-friendly materials.

Preparation

(a) 6-Bromo-3-methyl-3H-naphtho[1,2,3-de]quinoline-2,7-dione or 1-Bromo-4-(N-methylacetamido)anthraquinone and p-Methylaniline condensation; (b)N-(4-(p-toluidino)-9,10-dioxo-9,10-dihydroanthracen-1-yl)-N-methylacetamide closed loop into Anthrapyridone.

InChI:InChI=1/C24H18N2O2/c1-14-7-9-15(10-8-14)25-19-11-12-20-22-18(13-21(27)26(20)2)16-5-3-4-6-17(16)24(28)23(19)22/h3-13,25H,1-2H3

Synthetic route

6-hydroxy-3-methyl-3H-naphtho[1,2,3-de]quinoline-2,7-dione (2582-20-9) + p-toluidine (106-49-0) → 6-(p-Tolylamino)-N-methylanthrapyridone (81-39-0)

Conditions	Yield
With boric acid at 100 - 120℃; Large scale; Green chemistry;	97.5%

6-bromo-N-methylanthrapyridone (81-85-6) + p-toluidine (106-49-0) → 6-(p-Tolylamino)-N-methylanthrapyridone (81-39-0)

Conditions	Yield
With potassium acetate at 165℃;
With sodium acetate at 160 - 170℃;

3-methyl-6-nitro-3H-naphtho[1,2,3-de]quinoline-2,7-dione (873418-99-6) + p-toluidine (106-49-0) → 6-(p-Tolylamino)-N-methylanthrapyridone (81-39-0)

Conditions	Yield
With copper diacetate; sodium acetate at 160 - 175℃;

1-(acetyl-methyl-amino)-4-p-toluidino-anthraquinone (6535-64-4) → 6-(p-Tolylamino)-N-methylanthrapyridone (81-39-0)

Conditions	Yield
With sodium methylate

p-toluidine (106-49-0) + 1'-methyl-4-methoxy-anthrapyridone → 6-(p-Tolylamino)-N-methylanthrapyridone (81-39-0)

3-methyl-2,3-dihydro-7H-dibenzisoquinoline-2,7-dione (2582-19-6) → 6-(p-Tolylamino)-N-methylanthrapyridone (81-39-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: water; nitric acid 2: sodium acetate; copper (II)-acetate / 160 - 175 °C View Scheme

1-(acetyl-methyl-amino)-anthraquinone (75507-40-3) → 6-(p-Tolylamino)-N-methylanthrapyridone (81-39-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: water; KOH-solution; 2-ethoxy-ethanol 2: water; nitric acid 3: sodium acetate; copper (II)-acetate / 160 - 175 °C View Scheme

6-(p-Tolylamino)-N-methylanthrapyridone (81-39-0) → 2,8-Dimethyl-8H-benzonaphtho<1,2,3,4-lmn><4, 7>phenanthrolin-9-one (92629-03-3)

Conditions	Yield
With PPA at 175 - 180℃; for 6h;	99%
With sulfuric acid at 170℃;

6-(p-Tolylamino)-N-methylanthrapyridone (81-39-0) + acetic anhydride (108-24-7) → N-(3-methyl-2,7-dioxo-2,7-dihydro-3H-naphtho[1,2,3-de]quinolin-6-yl)-N-p-tolyl-acetamide (101611-82-9)

Conditions	Yield
With zinc(II) chloride

6-(p-Tolylamino)-N-methylanthrapyridone (81-39-0) → 3-methyl-6-(4-methyl-2-nitro-anilino)-3H-naphtho[1,2,3-de]quinoline-2,7-dione

Conditions	Yield
With nitric acid

6-(p-Tolylamino)-N-methylanthrapyridone (81-39-0) → 3-methyl-6-p-tolyl-3,6-dihydro-dibenzo[f,lmn][2,9]phenanthroline-2,7-dione (101812-37-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: ZnCl2 2: KOH View Scheme

Upstream product

• 81-85-6 6-bromo-N-methylanthrapyridone 
• 106-49-0 p-toluidine 
• 873418-99-6 3-methyl-6-nitro-3H-naphtho[1,2,3-de]quinoline-2,7-dione 
• 6535-64-4 1-(acetyl-methyl-amino)-4-p-toluidino-anthraquinone 
• 2582-19-6 3-methyl-2,3-dihydro-7H-dibenzisoquinoline-2,7-dione 
• 75507-40-3 1-(acetyl-methyl-amino)-anthraquinone 
• 2582-20-9 6-hydroxy-3-methyl-3H-naphtho[1,2,3-de]quinoline-2,7-dione 

Downstream Products

• 101812-37-7 3-methyl-6-p-tolyl-3,6-dihydro-dibenzo[f,lmn][2,9]phenanthroline-2,7-dione 
• 101611-82-9 1'-Methyl-4-(N-acetyl-p-toluidino)-anthrapyridon 

Relevant academic research and scientific papers

Environment-friendly synthesis method of anthrapyridone dye

The invention relates to an environment-friendly synthesis method of anthrapyridone dye. The method comprises the following steps: (1) adding ethyl acetate, monomethylamine and a phase transfer catalyst sequentially to a pressure vessel, and performing stirring for dissolution so as to obtain a first mixture; (2) heating the first mixture to 80-110 DEG C for a reaction, then performing cooling to40-70 DEG C, proceeding the reaction, performing pressure relief, determining the terminal point of the reaction, and performing cooling and filtration so as to obtain an intermediate A; (3) adding DMF, 1,4-dihydroxy anthraquinone and an auxiliary agent to the intermediate A, performing heating to 130-150 DEG C for a reaction, then performing cooling to 30-40 DEG C, and performing filtration so asto obtain an intermediate B; and (4) adding aromatic amine or alicyclic amine to the intermediate B, and performing a condensation reaction in the presence of boric acid until the terminal point. Through implementation of the environment-friendly synthesis method of anthrapyridone dye, good economic, social and ecologically environmental benefits can be achieved.

PIGMENT DISPERSION, AND RESIST COMPOSITION FOR COLOR FILTER AND INK COMPOSITION EACH USING THE PIGMENT DISPERSION

To provide a pigment dispersion excellent in dispersibility and spectral characteristics. The pigment dispersion at least includes: a dispersion medium; a compound represented by a general formula (1), the compound being dispersed in the dispersion medium; and a pigment having a quinacridone skeleton, the pigment being dispersed in the dispersion medium: General formula (1) in the general formula (1), R1 and R2 each independently represent a hydrogen atom, an alkyl group, an aryl group, or an aralkyl group.