2-Benzoyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile

Base Information

• Chemical Name: 2-Benzoyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile
• CAS No.: 10174-83-1
• Molecular Formula: C19H18 N2 O3
• Molecular Weight: 322.364
• Hs Code.: 2933499090
• DSSTox Substance ID: DTXSID50906583
• Wikidata: Q82875353
• Mol file: 10174-83-1.mol

Synonyms:2-benzoyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile;DTXSID50906583

Chemical Property of 2-Benzoyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile

Chemical Property:

• Vapor Pressure: 1.1E-11mmHg at 25°C
• Melting Point: 214-217oC
• Refractive Index: 1.6140 (estimate)
• Boiling Point: 539°Cat760mmHg
• Flash Point: 279.8°C
• PSA: 62.56000
• Density: 1.26g/cm³
• LogP: 2.90488
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 322.13174244
• Heavy Atom Count: 24
• Complexity: 494

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C2C(N(CCC2=C1)C(=O)C3=CC=CC=C3)C#N)OC
• Isomeric SMILES: COC1=C(C=C2[C@H](N(CCC2=C1)C(=O)C3=CC=CC=C3)C#N)OC

Technology Process of 2-Benzoyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile

There total 6 articles about 2-Benzoyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile 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: 85.0%

6,7-dimethoxy-3,4-dihydro-isoquinoline (3382-18-1) + sodium cyanide (143-33-9,25596-52-5) + benzoyl chloride (98-88-4) → (±)-2-benzoyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile (10174-83-1)

Guidance literature:

With sodium hydrogencarbonate; In dichloromethane; water; at 20 ℃; for 1.5h;

DOI:10.1007/s00706-004-0231-5

Reference yield: 42.0%

6,7-dimethoxy-3,4-dihydro-isoquinoline (3382-18-1) + potassium cyanide (151-50-8) + benzoyl chloride (98-88-4) → (±)-2-benzoyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile (10174-83-1)

Guidance literature:

N-benzyl-N,N,N-triethylammonium chloride; In dichloromethane; water; for 0.333333h; Irradiation; ultrasound sonication;

Reference yield: 40.0%

6,7-dimethoxy-3,4-dihydro-isoquinoline (3382-18-1) + benzoyl chloride (98-88-4) → N-(2-formyl-4,5-dimethoxyphenethyl)benzamide (23359-42-4) + (±)-2-benzoyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile (10174-83-1)

Guidance literature:

With sodium cyanide; In dichloromethane; water; for 4h; Ambient temperature;

upstream raw materials:

6,7-dimethoxy-3,4-dihydro-isoquinoline

sodium cyanide

benzoyl chloride

potassium cyanide

Downstream raw materials:

1-benzo[1,3]dioxol-5-ylmethyl-2-benzoyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline-1-carbonitrile

1-benzo[1,3]dioxol-4-ylmethyl-2-benzoyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic acid methyl ester

1-benzo[1,3]dioxol-4-ylmethyl-2-benzoyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic acid

4-(2-benzoyl-1-cyano-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-ylmethyl)nicotinic acid ethyl ester

Refernces

• 1、 Reimann, Eberhard,Grasberger, Fritz. "Protoberberines from Reissert- compounds. Part IX [1]. An alternative approach to dibenzoquinolizine- and isoquinonaphthyridin-13a-carboxylic acids, a novel synthesis of alangimarine". . p. 193 - 209. Retrieved 2007/10/03.
• 2、 Ezquerra, Jesus,Alvarez-Builla, Julio. "Organic Sonochemistry. Synthesis and Use of Reissert Compounds under PTC-Ultrasound". . p. 917 - 925. Retrieved 2007/10/02.