N-Methylcorydaldine

Base Information

• Chemical Name: N-Methylcorydaldine
• CAS No.: 6514-05-2
• Molecular Formula: C12H15 N O3
• Molecular Weight: 221.256
• Hs Code.: 2933790090
• NSC Number: 194246
• DSSTox Substance ID: DTXSID80307685
• Nikkaji Number: J146.915K
• Wikidata: Q27135873
• Metabolomics Workbench ID: 140101
• ChEMBL ID: CHEMBL504722
• Mol file: 6514-05-2.mol

Synonyms:N-methylcorydaldine

Chemical Property of N-Methylcorydaldine

Chemical Property:

• Vapor Pressure: 1.27E-06mmHg at 25°C
• Melting Point: 124-5°C
• Boiling Point: 400.4°Cat760mmHg
• Flash Point: 196°C
• PSA: 38.77000
• Density: 1.153g/cm³
• LogP: 1.26980
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 221.10519334
• Heavy Atom Count: 16
• Complexity: 269

Purity/Quality:

99% ^*data from raw suppliers

N-Methylcorydaldine ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC(=C(C=C2C1=O)OC)OC
• Description: An isoquinolone alkaloid, this base has been isolated from Thalictrum fendleri. It contains two methoxyl groups and one methylimino group. The structure has been determined by comparison with corydaldine (q.v.).

Technology Process of N-Methylcorydaldine

There total 11 articles about N-Methylcorydaldine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.0%

(2-bromo-3,4-dimethoxy-phenyl)-(6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydro-isoquinolin-1-yl)-methanone (247579-47-1) → 6,7-dimethoxy-N-methyl-2H-3,4-dihydroisoquinolin-1-one (6514-05-2) + 2-bromo-3,4-dimethoxybenzoic acid (71568-87-1)

Guidance literature:

With oxygen; In methanol; for 1h;

DOI:10.1021/jo982451w

Reference yield: 75.0%

6,7-dimethoxy-3,4-dihydro-2H-isoquinolin-1-one (493-49-2) + methyl iodide (74-88-4) → 6,7-dimethoxy-N-methyl-2H-3,4-dihydroisoquinolin-1-one (6514-05-2)

Guidance literature:

With sodium hydride; In benzene;

DOI:10.1246/cl.1980.875

Reference yield: 49.0%

7,8-Dimethoxy-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-1-on (899215-50-0) → 4,5-Dimethoxy-2-(2-methylaminoethyl)benzoesaeure + 6,7-dimethoxy-N-methyl-2H-3,4-dihydroisoquinolin-1-one (6514-05-2) + 4,5-Dimethoxy-2-[2-(N-methylformamido)ethyl]benzoesaeure (899215-52-2) + 2,3,4,5-tetrahydro-7,8-dimethoxy-3-methyl-1H-3-benzazepine-1,2-dione (124608-90-8)

Guidance literature:

With sodium periodate; In methanol; at 20 ℃; for 30h;

upstream raw materials:

Methyl fluorosulfonate

3,4-dimethoxyphenethyl isocyanate

6,7-dimethoxy-3,4-dihydro-2H-isoquinolin-1-one

methyl iodide

Downstream raw materials:

deoxyepinephrine

Refernces

• 1、 Orito, Kazuhiko,Miyazawa, Mamoru,Kanbayashi, Ryo,Tokuda, Masao,Suginome, Hiroshi. "Synthesis of phthalideisoquinoline and protoberberine alkaloids and indolo[2,1-α]isoquinolines in a divergent route involving palladium(0)- catalyzed carbonylation". . p. 6583 - 6596. Retrieved 2007/10/03.
• 2、 Joshi, Vidya,Hari, M. I.. "New Facile Synthesis of Isoquinolone Alkaloids". . p. 65 - 66. Retrieved 2007/10/02.