6514-05-2

Basic information

• Product Name: 2-Methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-one
• Synonyms: 2-Methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-one;3,4-Dihydro-6,7-dimethoxy-2-methyl-1(2H)-isoquinolinone;N-Methylcorydaldine
• CAS NO: 6514-05-2
• Molecular Formula: C₁₂H₁₅NO₃
• Molecular Weight: 221.2524
• Mol File: 6514-05-2.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 400.4°Cat760mmHg
• Flash Point: 196°C
• Appearance: /
• Density: 1.153g/cm³
• Vapor Pressure: 1.27E-06mmHg at 25°C
• Refractive Index: 1.54
• CAS DataBase Reference: 2-Methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-one(6514-05-2)
• EPA Substance Registry System: 2-Methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-one(6514-05-2)

Safety Data

• Hazardous Substances Data: 6514-05-2(Hazardous Substances Data)

Usage

Description

2-Methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-one is an isoquinolone alkaloid that has been isolated from Thalictrum fendleri. It contains two methoxyl groups and one methylimino group, and its structure has been determined by comparison with corydaldine.

Uses

Used in Pharmaceutical Industry:
2-Methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-one is used as a pharmaceutical compound for its potential therapeutic properties. Its unique structure and the presence of methoxyl and methylimino groups may contribute to its bioactivity and medicinal applications.
Used in Chemical Research:
This isoquinolone alkaloid is also used in chemical research for studying the structure, properties, and potential applications of isoquinolone derivatives. Its isolation from Thalictrum fendleri provides insights into the natural sources and biosynthesis of such compounds.

Synthesis Reference(s)

Tetrahedron Letters, 25, p. 3479, 1984 DOI: 10.1016/S0040-4039(01)91052-4

References

Dobbie, Lauder.,J. Chem. Soc., 67,17,20 (1895)

InChI:InChI=1/C12H15NO3/c1-13-5-4-8-6-10(15-2)11(16-3)7-9(8)12(13)14/h6-7H,4-5H2,1-3H3

Upstream product

• 421-20-5 Methyl fluorosulfonate 
• 35167-81-8 3,4-dimethoxyphenethyl isocyanate 
• 899215-50-0 7,8-Dimethoxy-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-1-on 
• 7647-01-0 hydrogenchloride 
• 482-74-6 cryptopine 
• 3947-79-3 1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-3,4-dihydroisoquinolinium iodide 
• 247579-47-1 (2-bromo-3,4-dimethoxy-phenyl)-(6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydro-isoquinolin-1-yl)-methanone 
• 1699-51-0 laudanosine 
• 83511-44-8 1-(2'-amino-4',5'-dimethoxy-α-oxobenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 493-49-2 6,7-dimethoxy-3,4-dihydro-2H-isoquinolin-1-one 
• 74-88-4 methyl iodide 

Downstream Products

• 501-15-5 deoxyepinephrine 

Relevant articles and documents

Indole cleavage with mebhydroline by sodium periodate - Part 2. Mechanism of the dilactam formation

The γ-carbolines 1a-d reacted with periodate by loss of one carbon - without available precursors - to the eight-membered dilactams 3a-c and the amino acid 9d. As possible intermediates of an indole cleavage α-aminoketones as models were examined. While the oxidation of chain-formed 13 afforded only a small amount of C-lost amide 23, the cyclic species 24 and 32 gave rise to considerably higher yields of the corresponding lactams 29 and 36. From the benzazepinone 32 with Hg(II)-EDTA the intermediate product 43, containing all genuine C-atoms, was formed, which could quantitatively cleaved by periodate to the lactam 36 and formic acid. This mechanism can be transferred to the reactions of the γ-carbolines 1a-d.

Fragmentation of Laudanosine by Single Electron Transfer Reactions

The radical cation of laudanosine, formed by a photoinduced electron transfer reaction or by oxidation with a tris(4-bromophenyl)aminium salt, undergoes cleavage of a C-C bond similar to the mass spectrometric fragmentation induced by electron ionization.

Hofmann Degradation of β-Hydroxy Ammonium Salts. α- and β-Hydroxylaudanosine, 7-Hydroxyglaucine, and 13-Hydroxyxylopinine

The four related β-hydroxy ammonium methiodide salts of α-hydroxylaudanosine (2a), β-hydroxylaudanosine (2b), 7-hydroxyglaucine (5a), and 13-hydroxyxylopinine (8a) have been subjected to Hofmann degradation.Although precedent dictates that such materials should form either epoxides or ketones, these are not found.Only products of (a) fragmentation and elimination (from 2a and 2b), (b) dehydration and elimination (from 5a), and (c) elimination and oxidation (from 8a) are obtained.The results are accounted for by consideration of the molecular geometries of theβ-hydroxy ammonium salts as experimentally determined from single-crystal X-ray studies and the geometric requirements for epoxide and ketone formation.