1010-68-0

Basic information

• Product Name: 1,3-Dihydro-5-hydroxy-1,3-dimethyl-2H-indol-2-one
• Synonyms: 4-Hydroxy-3,3-diMethylindolin-2-one;1,3-Dihydro-5-hydroxy-1,3-dimethyl-2H-indol-2-one;5-Hydroxy-1,3-dimethyl-2-indolinone;2H-Indol-2-one, 1,3-dihydro-5-hydroxy-1,3-diMethyl-;5-Hydroxy-1,3-dimethyl-1,3-dihydro-indol-2-one
• CAS NO: 1010-68-0
• Molecular Formula: C₁₀H₁₁NO₂
• Molecular Weight: 177.2
• Mol File: 1010-68-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 195-197 ºC
• Boiling Point: 410.1 °C at 760 mmHg
• Flash Point: 201.8 °C
• Appearance: /
• Density: 1.226
• PKA: 9.18±0.40(Predicted)
• CAS DataBase Reference: 1,3-Dihydro-5-hydroxy-1,3-dimethyl-2H-indol-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dihydro-5-hydroxy-1,3-dimethyl-2H-indol-2-one(1010-68-0)
• EPA Substance Registry System: 1,3-Dihydro-5-hydroxy-1,3-dimethyl-2H-indol-2-one(1010-68-0)

Safety Data

• Hazardous Substances Data: 1010-68-0(Hazardous Substances Data)

Usage

General Description

1,3-Dihydro-5-hydroxy-1,3-dimethyl-2H-indol-2-one is a chemical compound with the molecular formula C10H11NO2. It is a derivative of indole, a heterocyclic compound commonly found in plants. 1,3-Dihydro-5-hydroxy-1,3-dimethyl-2H-indol-2-one has a heterocyclic ring structure with a hydroxyl group and a methyl group, and it is known to have pharmacological properties, particularly as an inhibitor of enzymatic activity. It has been studied for its potential therapeutic effects in the treatment of neurodegenerative diseases and neurological disorders. Additionally, it has been investigated for its antioxidant and anti-inflammatory properties, making it a subject of interest in the field of medicinal chemistry.

Upstream product

• 5961-59-1 N-methyl-N-(4-methoxyphenyl)amine 
• 150-75-4 N-methyl-p-aminophenol 
• 3154-18-5 N-methyl-p-phenetidine 
• 153880-70-7 2-bromo-N-(4-ethoxy-phenyl)-N-methyl-propionamide 
• 161986-95-4 4-hydroxy-N-methyl-N-(α-bromopropionyl)aniline 
• 153880-69-4 N-(4-methoxyphenyl)-N-methyl-2-bromopropionylamide 
• 563-76-8 α-bromopropionyl bromide 

Downstream Products

• 57-47-6 (+/-)-Physostigmine 
• 65166-97-4 (-)-esermethole 
• 155795-39-4 (3S,1'S)-N-methyl-N-(1'-phenylethyl)-1,3-dimethyl-5-methoxyoxindol-3-ilacetamide 
• 159652-56-9 (+)-(3aR)-N¹-benzylnoreseroline phenylcarbamate 
• 164455-08-7 (+)-(3aR)-N¹-benzylnoreseromethole 
• 116707-99-4 1,3-dimethyl-5-methoxyindolin-2-one 
• 131057-63-1 1,3-dimethyl-5-ethoxyoxindole 

Relevant articles and documents

Agents useful for reducing amyloid precursor protein and treating demantia and methods of use thereof

The present invention provides compounds and methods of administering compounds to a subject taht can reduce βAPP production and that is not toxic in a wide range of dosages. The present invention also provides non-carbamate compounds and methods of administering such compounds to a subject that can reduce βAPP production and that is not tocix in a wide range of dosages. It has been discovered that either the racemic or enantiomerically pure non-carbamate compounds can be used to decrease βAPP production.

Process for preparing 1,3-dialkyl-5-hydroxyoxindoles and the ether derivatives thereof

The invention is directed to a process for preparing a 1,3-dialkyl-5-hydroxyoxindole of formula 1: STR1 comprising heating an N-alkyl-p-alkoxy-(α-haloacyl)anilide of formula 2: STR2 wherein the substituents are as defined herein, in the presence of an anhydrous zinc halide to a temperature in the range from about 120° C. to about 160° C., and isolating the 1,3-dialkyl-5-hydroxyoxindole prepared.

TOTAL SYNTHESIS OF RACEMIC PHYSOSTIGMINE, PHYSOVENINE AND ITS SULFUR ANALOGUE BY THE OXINDOLE-5-O-TETRAHYDROPYRANYL ETHER ROUTE

1,3-Dimethyl-5-tetrahydropyranyloxyoxindole (4) was synthesized from 4-methylaminophenol sulfate (metol) (1).Phase transfer catalyzed C3-alkylation of compound (4) produced alcohol (5), nitrile (8), and thioalkohol (13) after treatment of bromide (12) with thiourea.Compound (5) and (13) were converted into racemic physovenine (7) and thiaphysovenine (15) by reaction with LAH, in situ deprotection, and reaction of phenols with methyl isocyanate.Conversion of nitrile (8) into racemic physostigmine (11) which included a reductive N-methylation of 9 was similarly accomplished.