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

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

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

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.

Synthesis of phthalideisoquinoline and protoberberine alkaloids and indolo[2,1-α]isoquinolines in a divergent route involving palladium(0)- catalyzed carbonylation

6,7,3',4'-Alkoxy-substituted 1-(2'-bromobenzoyl)-3,4-dihydroisoquinoline methiodides 17 were treated with sodium borohydride in methanol or acetic acid to give erythro-1-(2'-bromo-α-hydroxybenzyl)-2-methyl-1,2,3,4- tetrahydroisoquinolines 19. Treatment of 17 with lithium aluminum hydride in tetrahydrofuran gave the threo-isomer 20 in preference to the erythro 19. On the basis of studies on palladium(0)-catalyzed carbonylation of 2-bromo-3,4- dimethoxybenzyl alcohol to 6,7-dimethoxyphthalide, amino alcohol 19 or 20 was treated with a catalytic amount of palladium(II) acetate and triphenylphosphine in an atmosphere of carbon monoxide in the presence of chlorotrimethylsilane and potassium carbonate in boiling toluene to give the corresponding erythro- or threo-types of phthalideisoquinoline alkaloids 1 or 2, respectively. One-pot cyclization of the erythro-amino alcohols 19 was achieved by heating in N,N-dimethylformamide containing potassium carbonate to give 2,3,8,9- or 2,3,9,10-alkoxy-substituted 5,6-dihydroindolo[2,1- α]isoquinolines 3, which have a unique tetracyclic skeleton characteristic of dibenzopyrrocoline alkaloids. Similarly, palladium-(0)-catalyzed carbonylation of 1-(2'-bromobenzyl)tetrahydroisoquinolines 21 in the presence of excess potassium carbonate was found to give 8-oxoberbines 22, which on reduction with lithium aluminum hydride can be converted to protoberberine alkaloids 4.

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.

New Facile Synthesis of Isoquinolone Alkaloids

Beckmann rearrangement of substituted indanone oximes (IIa, b) with PPA gives corydaldine (IIIa) and noroxyhydrastinine (IIIb) which on methylation yield N-methylcorydaldine (IVa) and N-methylnoroxyhydrastinine (IVb) respectively.

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.

FREMY'S SALT OXIDATION OF SOME ISOQUINOLINE ALKALOIDS. BIOGENETIC CONSIDERATIONS

Fremy's salt oxidation of benzylisoquinoline and aporphine alkaloids to isoquinolones and oxoaporphines is described.Aminium radicals are suggested to account for the observed results.Their possible involvement in alkaloid biosynthesis is considered.

NEW SYNTHESIS OF ISOQUINOLINE ALKALOIDS, THALIFOLINE, CORYPALLINE, AND CHERYLLINE

Isoquinoline alkaloids, thalifoline, corypalline, and cherylline, were synthesised by application of the cyclisation reaction of β-phenyl-ethyl isocyanate to N-methylisoquinoline lactam with Magic Methyl and the regioselective cleavage reaction of aromatic methoxyl groups with methionine and methanesulphanic acid.