61394-93-2

Usage

Uses

Used in Organic Chemistry:
4-NITRO-2,3-DIOXYINDOLE is used as a building block for the synthesis of complex molecules and materials with specific functionalities. Its unique structure allows for the creation of new compounds with potential applications in various industries.
Used in Material Science:
In the field of material science, 4-NITRO-2,3-DIOXYINDOLE is used for the development of new materials with specific properties. Its unique structure contributes to the design and synthesis of advanced materials for various applications.
Used in Pharmaceutical Research:
4-NITRO-2,3-DIOXYINDOLE is being investigated for its potential biological activities and pharmacological properties. Its unique structure and properties make it a promising candidate for the development of new drugs and therapeutic agents.
Used in Research and Development:
4-NITRO-2,3-DIOXYINDOLE holds promise for various applications in research and development. Its unique structure and properties make it a valuable tool for exploring new chemical reactions, synthesizing novel compounds, and developing innovative materials and technologies.

Synthetic route

indole-2,3-dione (91-56-5) → 4-nitro-1H-indole-2,3-dione (61394-93-2)

Conditions	Yield
With copper(II) nitrate In water; acetic acid for 0.025h; Nitration; microwave irradiation;	68%

3-nitroisonitrosoacetanilide (17122-61-1) → 4-nitro-1H-indole-2,3-dione (61394-93-2)

Conditions	Yield
With sulfuric acid at 50 - 80℃; for 20.1667h;	26%

4-nitro-1H-indole-2,3-dione (61394-93-2) + 1,3-cylohexanedione (504-02-9) + malononitrile (109-77-3) → C17H12N4O5

Conditions	Yield
With NiO nanoparticles on the graphitic carbon nitride nanosheets In ethanol at 80℃; for 0.0333333h;	95%

4-hydroxy[1]benzopyran-2-one (1076-38-6) + 4-nitro-1H-indole-2,3-dione (61394-93-2) + malononitrile (109-77-3) → C20H10N4O6

Conditions	Yield
With NiO nanoparticles on the graphitic carbon nitride nanosheets In ethanol at 80℃; for 0.0833333h;	93%

isatoic anhydride (118-48-9) + 4-nitro-1H-indole-2,3-dione (61394-93-2) + p-toluidine (106-49-0) → -nitro-3'-(p-tolyl)-1'H-spiro[indoline-3,2'-quinazoline]-2,4'(3'H)-dione

Conditions	Yield
With Tau In water for 6.5h; Reflux; Green chemistry;	90%

isatoic anhydride (118-48-9) + 4-nitro-1H-indole-2,3-dione (61394-93-2) + aniline (62-53-3) → C21H14N4O4

Conditions	Yield
With Tau In water for 6h; Reflux; Green chemistry;	89%

isatoic anhydride (118-48-9) + 4-nitro-1H-indole-2,3-dione (61394-93-2) + 4-methoxy-aniline (104-94-9) → 3'-(4-methoxyphenyl)-4-nitro-1'H-spiro[indoline-3,2'-quinazoline]-2,4'(3'H)-dione

Conditions	Yield
With Tau In water for 6h; Reflux; Green chemistry;	88%

4-nitro-1H-indole-2,3-dione (61394-93-2) + 3-(3-pyridinylmethylidene)-2-oxindole (3367-89-3) + (RS)-4-thiazolidinecarboxylic acid (444-27-9, 19291-02-2, 34592-47-7, 45521-09-3) → C25H19N5O4S

Conditions	Yield
In ethanol; water for 3h; Reflux;	73%

4-nitro-1H-indole-2,3-dione (61394-93-2) + 3-(3-pyridinylmethylidene)-2-oxindole (3367-89-3) + rac-Pro-OH (609-36-9) → C26H21N5O4

Conditions	Yield
In ethanol; water for 3h; Reflux;	66%

4-nitro-1H-indole-2,3-dione (61394-93-2) + L-phenylalanine (63-91-2) + 3-(3-pyridinylmethylidene)-2-oxindole (3367-89-3) → C30H23N5O4

Conditions	Yield
With air In ethanol; water for 3h; Reflux;	35%

4-nitro-1H-indole-2,3-dione (61394-93-2) + 4-hydrazinobenzene-1-sulfonamide hydrochloride (17852-52-7, 27918-19-0) → 4-[N'-(4-nitro-2-oxo-1,2-dihydro-indol-3-ylidene)hydrazino]benzenesulfonamide

Conditions	Yield
In ethanol for 2h; Heating;	33%

4-nitro-1H-indole-2,3-dione (61394-93-2) → 4-[N'-(4-Nitro-2-oxo-1,2-dihydro-indol-3-ylidene)-hydrazino]-benzenesulfonamide (222034-75-5, 388626-46-8)

Conditions	Yield
	33%

4-nitro-1H-indole-2,3-dione (61394-93-2) + acetophenone (98-86-2) → C17H14N2O5

Conditions	Yield
With pyrrolidine In ethanol for 3h; Reflux;	18%

3-indoxyl acetate (608-08-2) + 4-nitro-1H-indole-2,3-dione (61394-93-2) → 4-nitroindirubin (1257060-34-6)

Conditions	Yield
With toluene-4-sulfonic acid In ethanol at 65 - 70℃; for 3h;	15%

1'-naphthacetophenone (941-98-0) + 4-nitro-1H-indole-2,3-dione (61394-93-2) → C21H16N2O5

Conditions	Yield
With pyrrolidine In ethanol for 3h; Reflux;

1,4-benzodioxan-6-yl methyl ketone (2879-20-1) + 4-nitro-1H-indole-2,3-dione (61394-93-2) → C19H16N2O7

Conditions	Yield
With pyrrolidine In ethanol for 3h; Reflux;

4-nitro-1H-indole-2,3-dione (61394-93-2) + 4-ethylacetophenone (937-30-4) → C19H18N2O5

Conditions	Yield
With pyrrolidine In ethanol for 3h; Reflux;

4-nitro-1H-indole-2,3-dione (61394-93-2) + para-chloroacetophenone (99-91-2) → C17H13ClN2O5

Conditions	Yield
With pyrrolidine In ethanol for 3h; Reflux;

4-nitro-1H-indole-2,3-dione (61394-93-2) + para-bromoacetophenone (99-90-1) → C17H13BrN2O5

Conditions	Yield
With pyrrolidine In ethanol for 3h; Reflux;

4-nitro-1H-indole-2,3-dione (61394-93-2) + para-methylacetophenone (122-00-9) → C18H16N2O5

Conditions	Yield
With pyrrolidine In ethanol for 3h; Reflux;

4-nitro-1H-indole-2,3-dione (61394-93-2) + 1-(2,4-dichlorophenyl)ethan-1-one (2234-16-4) → C17H12Cl2N2O5

Conditions	Yield
With pyrrolidine In ethanol for 3h; Reflux;

4-nitro-1H-indole-2,3-dione (61394-93-2) + 1-(4-methoxyphenyl)ethanone (100-06-1) → C18H16N2O6

Conditions	Yield
With pyrrolidine In ethanol for 3h; Reflux;

4-nitro-1H-indole-2,3-dione (61394-93-2) + 3',4'-dichloroacetophenone (2642-63-9) → C17H12Cl2N2O5

Conditions	Yield
With pyrrolidine In ethanol for 3h; Reflux;

4-nitro-1H-indole-2,3-dione (61394-93-2) + 1-(3,4-dimethoxyphenyl)ethanone (1131-62-0) → C19H18N2O7

Conditions	Yield
With pyrrolidine In ethanol for 3h; Reflux;

4-nitro-1H-indole-2,3-dione (61394-93-2) + 4-phenyl-semicarbazide (537-47-3) → C15H11N5O4 (1380571-03-8)

Conditions	Yield
With acetic acid In ethanol Microwave irradiation;

Upstream product

• 91-56-5 indole-2,3-dione 
• 17122-61-1 3-nitroisonitrosoacetanilide 

Downstream Products

• 222034-75-5 4-[N'-(4-Nitro-2-oxo-1,2-dihydro-indol-3-ylidene)-hydrazino]-benzenesulfonamide 
• 1380571-03-8 C₁₅H₁₁N₅O₄ 

Relevant academic research and scientific papers

Method for preparing indole-2,3-dione derivatives by catalytic oxidation of microwave copper/peroxyacetic acid

The invention discloses a method for preparing indole-2,3-dione derivatives by catalytic oxidation of microwave copper/peroxyacetic acid. The method comprises the following steps: a catalytic amount of catalyst copper iodide, indole, a derivative of the indole and peroxyacetic acid are added into a reaction vessel, wherein the indole, the derivative of the indole and the peroxyacetic acid are usedas raw materials, ethanol is used as a solvent, the reaction vessel is placed into a microwave reaction instrument, a reaction is performed at certain temperature and power, after a certain time, reduced-pressure concentration is performed, and a product is purified by column chromatography. The method provided by the invention is a method having novel raw materials, simple operation and high efficiency used for preparing a benzimidazole derivative; and compared with the prior art, the method provided by the invention has an obviously-accelerated reaction speed than that under conventional heating, mild reaction conditions, simple operation, a high yield, safety, low costs and environmental protection.

Novel synthesis of 4-or 6-substituted indirubin derivatives

A simple and convenient route for synthesis of a series of 4-or 6-substituted indirubin derivatives by oxidation and subsequent condensation of indoxyl and isatin is described. Acidic reaction conditions are crucial to the condensation of 4-substituted derivatives, whereas for the condensation of 6-substituted derivatives, both acidic and basic conditions work well. Copyright Taylor & Francis Group, LLC.

Nitration of nitrogen heterocycles using microwaves

A comparative study of reaction time and yields for nitration of nitrogeneous heterocyclic compounds using Cu(NO3)2, KNO3 and NaNO3 under microwave irradiation as well as by conventional heating is reported.