51471-08-0

Basic information

• Product Name: 6,7-dihydro-1-Methyl-1H-indol-4(5H)-one
• Synonyms: 6,7-dihydro-1-Methyl-1H-indol-4(5H)-one;1-Methyl-6,7-dihydro-1H-indol-4(5H)-one;1-Methyl-1,5,6,7-tetrahydroindol-4-one;NSC 131678;1-Methyl-6,7-dihydroindol-4(5H)-one;1-methyl-4,5,6,7-tetrahydro-1H-indol-4-one;1,5,6,7-tetrahydro-1-methyl-4H-Indol-4-one;1-Methyl-6,7-dihydro-1H-indol-4(5H)
• CAS NO: 51471-08-0
• Molecular Formula: C₉H₁₁NO
• Molecular Weight: 149.18974
• Mol File: 51471-08-0.mol

Chemical Properties

• Melting Point: 84-86℃
• Boiling Point: 276℃
• Flash Point: 121℃
• Appearance: /
• Density: 1.17
• Vapor Pressure: 0.00489mmHg at 25°C
• Refractive Index: 1.598
• CAS DataBase Reference: 6,7-dihydro-1-Methyl-1H-indol-4(5H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6,7-dihydro-1-Methyl-1H-indol-4(5H)-one(51471-08-0)
• EPA Substance Registry System: 6,7-dihydro-1-Methyl-1H-indol-4(5H)-one(51471-08-0)

Safety Data

• Hazardous Substances Data: 51471-08-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6,7-dihydro-1-Methyl-1H-indol-4(5H)-one is used as an intermediate in the synthesis of various pharmaceuticals, particularly for the development of serotonin receptor agonists and antagonists. Its role in modulating neurotransmitter activity in the brain makes it a valuable component in the creation of medications targeting neurological and psychiatric disorders.
Used in Chemical Industry:
6,7-dihydro-1-Methyl-1H-indol-4(5H)-one also serves as a precursor for the production of various dyes and pigments, highlighting its utility in the chemical industry for creating a range of colorants used in different applications.
Used in Neurotransmitter Regulation:
6,7-dihydro-1-Methyl-1H-indol-4(5H)-one has been studied for its potential role in the regulation of neurotransmitter activity in the brain, which could lead to its use in the development of treatments for various neurological and psychiatric disorders, offering new therapeutic avenues for such conditions.

InChI:InChI=1/C9H11NO/c1-10-6-5-7-8(10)3-2-4-9(7)11/h5-6H,2-4H2,1H3

Upstream product

• 16806-93-2 4-oxo-4,5,6,7-tetrahydrobenzofuran 
• 74-89-5 methylamine 
• 96-54-8 N-Methylpyrrole 
• 96-48-0 4-butanolide 
• 35768-38-8 3-hydroxy-3,5,6,7-tetrahydro-2H-benzofuran-4-one 
• 504-02-9 1,3-cylohexanedione 
• 13754-86-4 1,5,6,7-tetrahydro-indol-4-one 
• 616-38-6 carbonic acid dimethyl ester 
• 122-07-6 N-(methyl)aminoacetaldehyde dimethyl acetal 
• 74-88-4 methyl iodide 

Downstream Products

• 905278-28-6 5'H-1,3-dibenzyl-6',7'-dihydro-1'-methylspiro(imidazolidin-5,4'-indole)-2,4-dione 
• 905278-37-7 C₂₅H₂₇N₃O₂ 
• 905278-45-7 5'H-3-benzyl-6',7'-dihydro-4-hydroxy-1'-methylspiro(imidazolidin-5,4'-indole)-2-one 
• 905278-29-7 5'H-3-benzyl-6',7'-dihydro-1'-methylspiro(imidazolidin-5,4'-indole)-2,4-dione 

Relevant articles and documents

β-selective C-H arylation of pyrroles leading to concise syntheses of lamellarins C and I

The first general β-selective C-H arylation of pyrroles has been developed by using a rhodium catalyst. This C-H arylation reaction, which is retrosynthetically straightforward but results in unusual regioselectivity, could result in de novo syntheses of

Formation of N-substituted 4- and 7-oxo-4,5,6,7-tetrahydroindoles revisited: A mechanistic interpretation and conversion into 4- and 7-oxoindoles

An efficient method for the preparation of 4-oxo-4,5,6,7-tetrahydroindoles was successfully applied to the synthesis of N-substituted 7-oxo-4,5,6,7- tetrahydroindoles for the first time. Both isomers where converted into their corresponding 4- and 7-oxoindoles in good yields utilizing a novel aromatization protocol. Based on the impurity profile obtained, however, different mechanisms for the formation of the 4- and 7-oxo-4,5,6,7-tetrahydroindole derivatives are discussed. In addition, the reaction sequences appear to be stereospecific allowing for the direct introduction of a chiral center α to the nitrogen and preparation of enantiomerically enriched products.

NOVEL ANTIVIRAL COMPOUNDS

The present invention relates to a compound of formula I: or a pharmaceutically acceptable salt thereof, wherein the symbols are as defined in the specification; a pharmaceutical composition comprising the same, a method for treating or preventing a viral infection such as HIV using the same.

Green N-methylation of electron deficient pyrroles with dimethylcarbonate

The N-methylation of electron-deficient pyrroles was affected using dimethyl carbonate in the presence of DMF and catalytic DABCO. This alkylation methodology has proven useful for the alkylation of a variety of pyrroles in 72-98% yields and is considered to be green chemistry relative to the more common use of methyl halides or dimethyl sulfate.

A dichotomy in the Friedel-Crafts reaction of lactones provides a convenient new route to 2-acylated pyrroles and tetrahydroindolones

In striking contrast to arenes, N-methylpyrrole undergoes Friedel-Crafts acylation with lactones. The reaction is most efficient with γ- and δ-lactones; ε-lactones proceed with poor overall conversion while β-lactones display poor selectivity. γ-Alkyl-γ-lactones readily yield 4,5,6,7-tetrahydroindol-7-ones through a sequence analogous to the Truce-Olson annulation.

A FACILE SYNTHESIS OF 4-OXO-4,5,6,7-TETRAHYDROINDOLES

Condensation of 1,3-cyclohexanedione with chloroacetaldehyde followed by dehydration gave 4-oxo-4,5,6,7-tetrahydrobenzofuran in a good yield.The tetrahydrobenzofuran was quantitatively converted into 4-oxo-4,5,6,7-tetrahydroindoles.