20870-77-3

Usage

Uses

Used in Pharmaceutical Industry:
4-CHLORO-1,3-DIHYDRO-INDOL-2-ONE is used as a building block in the synthesis of pharmaceutical drugs and organic compounds. Its unique structure and properties make it a valuable component in the development of new medications and therapeutic agents.
Used in Organic Synthesis:
4-CHLORO-1,3-DIHYDRO-INDOL-2-ONE is utilized as an important intermediate in organic synthesis, allowing for the creation of a wide range of chemical compounds and materials. Its versatility and reactivity contribute to its significance in this field.

InChI:InChI=1/C8H6ClNO/c9-6-2-1-3-7-5(6)4-8(11)10-7/h1-3H,4H2,(H,10,11)

Upstream product

• 97522-09-3 methyl 2-(2-chloro-6-nitrophenyl)acetate 
• 10565-17-0 (2-Chlor-6-nitro-phenyl)-malonsaeure-diaethylester 
• 6344-05-4 4-chloroisatin 
• 828-68-2 4-chloro-3-hydrazonooxindole 
• 89277-98-5 2-(2-chloro-6-nitrophenyl)acetonitrile 
• 36892-19-0 (2-chloro-6-nitro-phenyl)-pyruvic acid 
• 108-42-9 3-chloro-aniline 
• 129822-39-5 N-(tert-butoxycarbonyl)-2-amino-6-chlorotoluene 
• 87-60-5 3-chloro-2-methylbenzenamine 
• 147124-36-5 1,3-dimethyl 2-(2-chloro-6-nitrophenyl)propanedioate 
• 3209-22-1 1,2-Dichloro-3-nitrobenzene 
• 100376-53-2 2-(2-amino-6-chlorophenyl)ethyl alcohol 
• 138343-82-5 (2-tert-Butoxycarbonylamino-6-chloro-phenyl)-acetic acid 
• 2564-05-8 2-chloro-N-(3-chlorophenyl)acetamide 

Downstream Products

• 83254-81-3 1-phenyl-4-chlorooxindole 
• 1637752-36-3 4'-chlorospiro[cyclopropane-1,3'-indoline]-2'-one 
• 23709-54-8 3-Benzyl-4-chlor-2-indolinon 
• 1398681-41-8 benzaldehyde O-3-benzyl-4-chloro-2-oxoindolin-3-yl oxime 
• 1398681-72-5 3-benzyl-3-bromo-4-chloroindoline-2-one 
• 1374637-23-6 4'-chloro-2,6-diphenylspiro[cyclohexane-1,3'-indoline]-2',4-dione 
• 41910-64-9 4-chloroindoline 

Relevant academic research and scientific papers

A novel methodology for the efficient synthesis of 3-monohalooxindoles by acidolysis of 3-phosphate-substituted oxindoles with haloid acids

A novel method for the synthesis of 3-monohalooxindoles by acidolysis of isatin-derived 3-phosphate-substituted oxindoles with haloid acids was developed. This synthetic strategy involved the preparation of 3-phosphate-substituted oxindole intermediates and SN1 reactions with haloid acids. This new procedure features mild reaction conditions, simple operation, good yield, readily available and inexpensive starting materials, and gram-scalability.

A Benzisoelenazolone modified pyrrole methyl ester substituted indole ketone compound and use thereof

The invention discloses a benzisoselenazolone-modified pyrrolyl formate-substituted indolone compound and a use thereof. The invention depends on and claims the priority of a Chinese patent application 201110105248.0 submitted on April 26, 2011. Through reference, all contents of the Chinese patent application 201110105248.0 are incorporated into the invention. The benzisoselenazolone-modified pyrrolyl formate-substituted indolone compound is shown in the general formula I. The 2-indolone compound provided by the invention has excellent antitumor activity and can be widely used for preparation of antitumor drugs.

Selective reduction of carbonyl groups in the presence of low-valent titanium reagents

The chemoselective reduction of several structurally diverse compounds containing carbonyl groups was achieved in the presence of low-valent titanium reagents. This novel synthetic method provides easy access to highly selective reduction of carbonyl groups, and possesses several advantages including one-step procedure, convenient manipulation, good to excellent yields, and short reaction times.

Synthesis of indolones and quinolones by reductive cyclisation of o-nitroaryl acids using zinc dust and ammonium formate

A novel protocol for the synthesis of indolone and quinolone derivatives from o-nitroaryl acids was developed using Zn and HCO2NH4 under supercritical fluid carbon dioxide (scCO2) medium. The process involves the reduction of the nitro group to an amino group followed by in situ cyclisation.

Synthesis of five-, six-, and seven-membered ring lactams by Cp*Rh complex-catalyzed oxidative N-heterocyclization of amino alcohols

A new effective catalytic system consisting of [Cp*RhCl 2]2/K2CO3 (Cp* = pentamethylcyclopentadienyl) for the lactamization of amino alcohols has been developed. As an example, the reaction of 3-(2-aminophenyl)-1-propanol in the presence of [Cp*RhCl2]2 (5.0% Rh) and K 2CO3 (10%) in acetone gives 3,4-dihydro-2(1H)-quinolinone in an isolated yield of 80%. A variety of five-, six-, and seven-membered benzo-fused lactams are synthesized by this catalytic system.

An improved procedure for the regiospecific synthesis of electron deficient 4- and 6-substituted isatins

The regiospecific synthesis of 4- and 6-substituted isatins 5a-g in four steps from halonitrobenzenes 1a-g has been investigated for a variety of substrates (Scheme 1). The procedure makes use of readily available, easily handled materials and in most cases purification of neither intermediates nor final products is required. Yields of isatins are between 26 and 75% (Table 1). Improved yields of known isatins are reported as well as the syntheses of previously unreported isatins. This method, taken together with known procedures, provides for the synthesis of the full complement of isatin regioisomers.

A general oxindole synthesis

A general synthesis of indol-2(3H)-ones (oxindoles), was developed based on the addition of dimethyl malonate to commercially available halonitrobenzenes. The advantage of this route over many other oxindole syntheses was the regiochemical control of the substitution pattern on the aromatic ring.

Preparation of indoles and oxindoles from N-(tert-butoxycarbonyl)-2-alkylanilines

Treatment of dilithiated N-(tert-butoxycarbonyl)anilines 1 with dimethylformamide or carbon dioxide furnishes intermediates 3, 5, that are easily converted to N-(tert-butoxycarbonyl)indoles 4 and oxindoles (indol-2(3H)-ones, 7), respectively. Condensation of dilithiated 1 with N-methoxy-N-methylamides provides ketones 9 which are cyclized upon trifluoroacetic acid treatment to either 2-substituted 1-(tert-butoxycarbonyl)indoles 10 or 2-substituted indoles 11 depending on the reaction time. This general methodology has been applied to efficient synthesis of 1,2-alkyl-bridged indoles 12, 1,3,4,5-tetrahydrobenz[c,d]indole (16), 2a,3,4,5-tetrahydrobenz[c,d]indol-2(1H)-one (18), and 1-(tert-butoxycarbonyl)1H-pyrrolo[2,3-b]pyridine (21).

1,3-dicarboxamide-oxindoles as antiinflammatory agents

1,3-Dicarboxamidooxindoles as antiinflammatory agents prepared by reaction of the 1-carbamoyloxindole with an isocyanate or by aminolysis of the corresponding alkyl 1-carbamoyloxindole-3-carboxylate.