7-Hydroxy-6-methoxy-3,4-dihydroisoquinoline

Base Information

• Chemical Name: 7-Hydroxy-6-methoxy-3,4-dihydroisoquinoline
• CAS No.: 4602-73-7
• Molecular Formula: C10H11 N O2
• Molecular Weight: 177.203
• Hs Code.: 29335995
• Mol file: 4602-73-7.mol

Synonyms:6-Methoxy-7-hydroxy-3,4-dihydroisoquinoline;7-Hydroxy-6-methoxy-3,4-dihydroisoquinoline; NSC 627589

Chemical Property of 7-Hydroxy-6-methoxy-3,4-dihydroisoquinoline

Chemical Property:

• Appearance/Colour: yellow crystalline powder and flakes
• Vapor Pressure: 7.74E-05mmHg at 25°C
• Melting Point: 187-191 ºC
• Boiling Point: 332.1ºC at 760 mmHg
• PKA: 9.73±0.20(Predicted)
• Flash Point: 154.6ºC
• PSA: 41.82000
• Density: 1.26g/cm3
• LogP: 0.81140
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: SOLUBLE IN HOT WATER

Purity/Quality:

99% ^*data from raw suppliers

7-Hydroxy-6-methoxy-3,4-dihydroisoquinoline(~90%byHPLC) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 36/38-21/22
• Safety Statements: 36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 7-Hydroxy-6-methoxy-3,4-dihydroisoquinoline acts as a reagent for the synthesis and dual dopamine D1 receptor agonist/D2 receptor antagonist activity, and SAR of tetrahydroisoquinolines for treating schizophrenia.

Technology Process of 7-Hydroxy-6-methoxy-3,4-dihydroisoquinoline

There total 5 articles about 7-Hydroxy-6-methoxy-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: 64.0%

6,7-dimethoxy-3,4-dihydro-isoquinoline (3382-18-1) → 3,4-dihydro-7-hydroxy-6-methoxy-isoquinoline (4602-73-7)

Guidance literature:

With hydrogen bromide; at 95 ℃; for 15h;

DOI:10.1021/jo00380a024

Reference yield:

N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]formamide (282721-32-8) → 3,4-dihydro-7-hydroxy-6-methoxy-isoquinoline (4602-73-7)

Guidance literature:

N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]formamide; With trichlorophosphate; In acetonitrile; for 4h; Inert atmosphere; Reflux;

With ammonium hydroxide; In water;

Reference yield:

2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) → 3,4-dihydro-7-hydroxy-6-methoxy-isoquinoline (4602-73-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 175 °C / Inert atmosphere

1.2: 95 °C / Inert atmosphere

2.1: hydrogen bromide / 95 °C / Inert atmosphere

With hydrogen bromide; 1.2: |Bischler-Napieralski Reaction;

DOI:10.1016/j.tetlet.2020.151924

upstream raw materials:

N-formyl-2-[3-methoxy-4-(benzyloxy)phenyl]ethylamine

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

N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]formamide

2-(3,4-dimethoxyphenyl)-ethylamine

Downstream raw materials:

(7-Hydroxy-6-methoxy-1,2,3,4-tetrahydro-isoquinolin-1-yl)-acetic acid

(7-Hydroxy-6-methoxy-1,2,3,4-tetrahydro-isoquinolin-1-yl)-acetic acid ethyl ester

Refernces

• 1、 Arai, Masayoshi,Han, Chisu,Jacobs, William R.,Kamiya, Kentaro,Kotoku, Naoyuki,Setiawan, Andi,Sumii, Yuji,Vilchèze, Catherine. "3-(Phenethylamino)demethyl(oxy)aaptamine as an anti-dormant mycobacterial substance: Isolation, evaluation and total synthesis". . . Retrieved 2020/04/24.
• 2、 Pelletier, Jeffrey C.,Cava, Michael P.. "Synthesis of the Marine Alkaloids Aaptamine and Demethyloxyaaptamine and of the Parent Structure Didemethoxyaaptamine". . p. 616 - 622. Retrieved 2007/10/02.