1-(5-Chloro-2-nitrophenyl)-6,7-dimethoxy-3,4-dihydroisoquinoline

Base Information

• Chemical Name: 1-(5-Chloro-2-nitrophenyl)-6,7-dimethoxy-3,4-dihydroisoquinoline
• CAS No.: 62206-13-7
• Molecular Formula: C17H15ClN2O4
• Molecular Weight: 346.77
• DSSTox Substance ID: DTXSID20370939
• Wikidata: Q82158128
• Mol file: 62206-13-7.mol

Synonyms:62206-13-7;1-(5-Chloro-2-nitrophenyl)-3,4-dihydro-6,7-dimethoxyisoquinoline;1-(5-chloro-2-nitrophenyl)-6,7-dimethoxy-3,4-dihydroisoquinoline;DTXSID20370939;AKOS015911383;FT-0605789;A833641;1-(5-Chloro-2-nitrophenyl)-3,4-dihydro-6,7dimethoxyisoquinoline

Chemical Property of 1-(5-Chloro-2-nitrophenyl)-6,7-dimethoxy-3,4-dihydroisoquinoline

Chemical Property:

• Vapor Pressure: 1.99E-09mmHg at 25°C
• Melting Point: 169 °C
• Refractive Index: 1.625
• Boiling Point: 494.3 °C at 760 mmHg
• PKA: 4.40±0.20(Predicted)
• Flash Point: 252.7 °C
• PSA: 76.64000
• Density: 1.37 g/cm³
• LogP: 3.61770
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 346.0720347
• Heavy Atom Count: 24
• Complexity: 496

Purity/Quality:

98%min ^*data from raw suppliers

1-(5-CHLORO-2-NITROPHENYL)-6,7-DIMETHOXY-3,4-DIHYDROISOQUINOLINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C2C(=C1)CCN=C2C3=C(C=CC(=C3)Cl)[N+](=O)[O-])OC

Technology Process of 1-(5-Chloro-2-nitrophenyl)-6,7-dimethoxy-3,4-dihydroisoquinoline

There total 3 articles about 1-(5-Chloro-2-nitrophenyl)-6,7-dimethoxy-3,4-dihydroisoquinoline 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: 72.0%

5-chloro-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-nitrobenzamide (301174-19-6) → 6,7-dimethoxy-1-(5'-chloro-2'-nitrophenyl)-3,4-dihydroisoquinoline (62206-13-7)

Guidance literature:

With phosphorus pentoxide; trichlorophosphate; In xylene; for 3h; Heating;

DOI:10.1016/j.tet.2004.08.026

Reference yield:

5-chloro-2-nitrobenzoic acid (2516-95-2) → 6,7-dimethoxy-1-(5'-chloro-2'-nitrophenyl)-3,4-dihydroisoquinoline (62206-13-7)

Guidance literature:

Multi-step reaction with 3 steps

1: thionyl chloride / benzene / 12 h / 70 - 75 °C

2: pyridine / benzene / 20 °C

3: POCl₃ / acetonitrile / Heating

With pyridine; thionyl chloride; trichlorophosphate; In acetonitrile; benzene; 3: Bischler-Napieralski reaction;

DOI:10.1016/j.ejmech.2006.03.011

Reference yield:

5-chloro-2-nitrobenzoyl chloride (41994-44-9) → 6,7-dimethoxy-1-(5'-chloro-2'-nitrophenyl)-3,4-dihydroisoquinoline (62206-13-7)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / benzene / 20 °C

2: POCl₃ / acetonitrile / Heating

With pyridine; trichlorophosphate; In acetonitrile; benzene; 2: Bischler-Napieralski reaction;

DOI:10.1002/jccs.200500135 DOI:10.1016/j.ejmech.2006.03.011

upstream raw materials:

5-chloro-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-nitrobenzamide

5-chloro-2-nitrobenzoic acid

5-chloro-2-nitrobenzoyl chloride

Downstream raw materials:

4-chloro-2-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)aniline

6,7-dimethoxy-1-(5-chloro-2-aminophenyl)-1,2,3,4-tetrahydroisoquinoline

Refernces

• 1、 Kuo, Chen-Yuan,Wu, Ming-Jung. "A novel synthesis of 5,6-dihydroindazolo[3,2-a]isoquinolines and their relative compounds via tin(II) chloride dihydrate as reducing agent". . p. 965 - 974. Retrieved 2007/10/03.