24331-94-0

Basic information

• Product Name: 1,4-Dihydro-3(2H)-isoquinolinone
• Synonyms: 1,4-DIHYDRO-3(2H)-ISOQUINOLINONE;1,4-DIHYDRO-2H-ISOQUINOLIN-3-ONE;3(2H)-Isoquinolinone, 1,4-dihydro-;1,2,3,4-Tetrahydroisoquinolin-3-one;1,2-Dihydroisoquinoline-3(4H)-one;1,4-dihydroisoquinolin-3(2H)-one;1,2-dihydroisoquinolin-3(4H)-one
• CAS NO: 24331-94-0
• Molecular Formula: C₉H₉NO
• Molecular Weight: 147.17
• EINECS: 246-174-3
• Product Categories: pharmacetical
• Mol File: 24331-94-0.mol
• Article Data: 19

Chemical Properties

• Melting Point: 146-148 °C
• Boiling Point: 370.61 °C at 760 mmHg
• Flash Point: 215.874 °C
• Appearance: /
• Density: 1.143 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.564
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 16.35±0.20(Predicted)
• CAS DataBase Reference: 1,4-Dihydro-3(2H)-isoquinolinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Dihydro-3(2H)-isoquinolinone(24331-94-0)
• EPA Substance Registry System: 1,4-Dihydro-3(2H)-isoquinolinone(24331-94-0)

Safety Data

• Hazardous Substances Data: 24331-94-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 107, p. 435, 1985 DOI: 10.1021/ja00288a027

InChI:InChI=1/C9H9NO/c11-9-5-7-3-1-2-4-8(7)6-10-9/h1-4H,5-6H2,(H,10,11)

Upstream product

• 615-13-4 2-indanone 
• 40851-66-9 2-(tert-butoxycarbonylaminomethyl)phenylacetic acid 
• 6291-06-1 N-Hydroxymethylphenylacetic acid amide 
• 94286-13-2 (2-aminomethyl-phenyl)-acetic acid ethyl ester 
• 7651-81-2 3-isoquinolinol 
• 56023-50-8 methyl 2-(2-azidomethyl)phenyl acetate 
• 112072-92-1 [2-(acetylamino-methyl)-phenyl]-acetic acid 
• 63969-83-5 2-formylphenylacetic acid methyl ester 
• 119-65-3 isoquinoline 
• 100-46-9 benzylamine 
• 79388-18-4 N-Benzyl-2-methanesulfinyl-acetamide 
• 18813-51-9 Methylmercaptoessigsaeure-benzylamid 
• 138350-83-1 N-(tert-butoxycarbonyl)-2-methylbenzylamine 
• 57058-32-9 N-(2-chlorobenzyl)acetamide 

Downstream Products

• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 4370-95-0 3-amino-2-phenyl-propionic acid 
• 52067-92-2 2-[2-(aminomethyl)-phenyl]acetic acid hydrochloride 
• 885270-67-7 7-amino-1,4-dihydroisoquinolin-3(2H)-one 
• 120285-29-2 3-chloroisoquinoline-4-carbaldehyde 
• 1402830-68-5 (+)-tert-butyl 3-(2-oxo-2-phenylethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 103681-50-1 10a-Dimethylamino-1,2-diphenyl-3-oxo-10,10a-dihydro-3H,5H-pyrrolo<1,2-b>isochinolin 
• 103681-57-8 3,5-Dioxo-1,2-diphenyl-3H,5H-pyrrolo<1,2-b>isochinolin 
• 103681-65-8 1,2-Diphenyl-3-oxo-3H,5H-pyrrolo<1,2-b>isochinolin 
• 143266-06-2 4-benzoyl-3-ethoxy-1,4-dihydro-4-methylisoquinoline 
• 146645-31-0 4-Benzyl-3,3-dideutero-2-methyl-1,2,3,4-tetrahydroisochinolin 
• 143265-95-6 3-ethoxy-1,4-dihydro-4-hydroxymethyl-4-methylisoquinoline 
• 143266-13-1 4,5-dimethyl-3-ethoxy-1H-2-benzazepine 
• 143265-98-9 3-ethoxy-5-methyl-1H-2-benzazepine 

Relevant articles and documents

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The Synthesis of N-Heterocycles using ortho-Metallated Primary Benzylamine Complexes of Palladium(II) and Platinum(II)

The synthesis of the isoindolinimines (5) by the insertion of isocyanides into the metal-carbon bond of the ortho-palladated primary benzylamine complex (1a) is described; the novel oxidative addition and subsequent reductive elimination of the ortho-metallated primary benzylamine-platinum complex (6) yields 3-oxo-1,2,3,4-tetrahydroisoquinoline (8).

Synthetic approaches to N- and 4-substituted 1,4-dihydro-3(2H)-isoquinolinone derivatives

Reaction of methyl-2-(2-formylphenyl)acetate with primary amines in a reductive amination/cyclisation process resulted in N-substituted 1,4-dihydro-3(2H)-isoquinolinones. With H2NCH2R sodium borohyride is a suitable reductant (11 examples), but H2NCHR1R2 required a transfer hydrogenation using ammonium formate catalysed by palladium on carbon (9 examples). 4-Substituted-1,4-dihydro-3(2H)-isoquinolinones were synthesised by deprotonation (n-butyllithium) and addition of R3CH2Br (12 examples with R3 = alkyl, Ar, CH[dbnd]CH2, C[tbnd]CH). Modest diastereoselectivity was achieved with 1,4-dihydro-3(2H)-isoquinolinones derived from H2NCHMeR2 [R2 = (η5-C5H4)Co(η4-C4Ph4) - max. dr = 1.9 : 1], but use of H2NCHMeFc (Fc = ferrocenyl) provided a new method of 1,4-dihydro-3(2H)-isoquinolinone N-deprotection with formic acid.

Desymmetrization of Prochiral Cyclopentenes Enabled by Enantioselective Palladium-Catalyzed Oxidative Heck Reaction

In the presence of a catalytic amount of Pd(TFA)2 and a chiral Pyox ligand under oxygen atmosphere, oxidative Heck reaction between arylboronic acids and 4-substituted or 4,4-disubstituted cyclopent-1-enes afforded the chiral arylated products with concurrent creation of two stereocenters in good yields with excellent diastereo- and enantioselectivities.