6798-05-6

Basic information

• Product Name: 2-Methyl-1,4-dihydroisoquinolin-3(2H)-one
• Synonyms: 2-Methyl-1,4-dihydroisoquinolin-3(2H)-one;2-methyl-1,2-dihydroisoquinolin-3(4H)-one;2-methyl-1,2,3,4-tetrahydroisoquinolin-3-one
• CAS NO: 6798-05-6
• Molecular Formula: C₁₀H₁₁NO
• Molecular Weight: 161.20044
• Mol File: 6798-05-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 323.5°C at 760 mmHg
• Flash Point: 133.8°C
• Appearance: /
• Density: 1.12g/cm³
• Vapor Pressure: 0.00026mmHg at 25°C
• Refractive Index: 1.564
• CAS DataBase Reference: 2-Methyl-1,4-dihydroisoquinolin-3(2H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-1,4-dihydroisoquinolin-3(2H)-one(6798-05-6)
• EPA Substance Registry System: 2-Methyl-1,4-dihydroisoquinolin-3(2H)-one(6798-05-6)

Safety Data

• Hazardous Substances Data: 6798-05-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H11NO/c1-11-7-9-5-3-2-4-8(9)6-10(11)12/h2-5H,6-7H2,1H3

Upstream product

• 1334292-32-8 1-(2-(bromomethyl)phenyl)propan-2-one 
• 51052-00-7 1-(2-methylphenyl)acetone 
• 1334292-89-5 1-(2-(azidomethyl)phenyl)propan-2-one 

Downstream Products

• 1357254-43-3 C₁₆H₁₄ClNO 
• 25771-98-6 4-(4-chlorophenyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 1357254-49-9 C₁₉H₁₆N₂O 
• 1357254-40-0 C₁₉H₁₈N₂ 
• 135182-06-8 4-(4-Methoxy-phenyl)-2-methyl-1,4-dihydro-2H-isoquinolin-3-one 
• 1357254-47-7 C₁₉H₂₁NO 
• 1357254-39-7 C₁₉H₂₃N 
• 1357254-38-6 C₁₇H₁₉N 
• 1357254-36-4 C₁₇H₁₉N 
• 1357254-46-6 C₁₇H₁₇NO 
• 1357254-37-5 C₁₇H₁₉NO₂S 
• 1357254-44-4 C₁₆H₁₄FNO 

Relevant articles and documents

Overcoming product inhibition in catalysis of the intramolecular Schmidt reaction

A method for carrying out the intramolecular Schmidt reaction of alkyl azides and ketones using a substoichiometric amount of catalyst is reported. Following extensive screening, the use of the strong hydrogen-bond-donating solvent hexafluoro-2-propanol was found to be consistent with low catalyst loadings, which ranged from 2.5 mol % for favorable substrates to 25 mol % for more difficult cases. Reaction optimization, broad substrate scope, and preliminary mechanistic studies of this improved version of the reaction are described.

Palladium-Catalyzed Inter- and Intramolecular α-Arylation of Amides. Application of Intramolecular Amide Arylation to the Synthesis of Oxindoles

2A palladium-catalyzed α-arylation of amides is reported. Intermolecular arylation of N,N-dimethylamides and lactams occurs using aryl halides, silylamide base, and a palladium catalyst. Intramolecular arylation of N-(2-halophenyl)amides occurs using alkoxide base and a palladium catalyst. The palladium catalyst was formed in situ from Pd(dba)2 (dba = trans,trans-dibenzylidene acetone) and BINAP (2,2′-bis(diphenylphosphino)-1,1′-binaphthalene). Although the intermolecular arylation of amides is less general than that reported previously for ketones, unfunctionalized and electron-rich aryl halides gave α-arylamides in 48-75% yield and N-methyl-α-phenylpyrrolidinone in 49% yield. These reactions provided the highest yields yet reported for regioselective amide arylations. Intramolecular amide arylation of 2-bromoanilides gave oxindoles in 52-82% yield. Mono- and disubstituted acetanilides gave 1,3-di- and 1,3,3-trisubstituted oxindoles. The use of dioxane, rather than THF, solvent was important for some of the amide arylations.