4-(3,4-dihydroxyphenyl)-7-hydroxy-8-methyl-1,2,3,4-tetrahydroisoquinoline

Base Information

• Chemical Name: 4-(3,4-dihydroxyphenyl)-7-hydroxy-8-methyl-1,2,3,4-tetrahydroisoquinoline
• CAS No.: 139233-51-5
• Molecular Formula: C₁₆H₁₇NO₃*ClH
• Molecular Weight: 307.777
• Mol file: 139233-51-5.mol

Synonyms:4-(3,4-dihydroxyphenyl)-7-hydroxy-8-methyl-1,2,3,4-tetrahydroisoquinoline

Chemical Property of 4-(3,4-dihydroxyphenyl)-7-hydroxy-8-methyl-1,2,3,4-tetrahydroisoquinoline

Chemical Property:

• Vapor Pressure: 3.31E-11mmHg at 25°C
• Boiling Point: 514.5°Cat760mmHg
• Flash Point: 204.5°C
• PSA: 72.72000
• Density: 1.304g/cm³
• LogP: 2.67570

Purity/Quality:

4-(3,4-DIHYDROXYPHENYL)-7-HYDROXY-8-METHYL-1,2,3,4-TETRAHYDROISOQUINOLINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-(3,4-dihydroxyphenyl)-7-hydroxy-8-methyl-1,2,3,4-tetrahydroisoquinoline

There total 8 articles about 4-(3,4-dihydroxyphenyl)-7-hydroxy-8-methyl-1,2,3,4-tetrahydroisoquinoline 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:

3-methoxy-2-methylbenzoyl chloride (24487-91-0) → (R)-(-)-4-(3,4-dihydroxyphenyl)-7-hydroxy-8-methyl-1,2,3,4-tetrahydroisoquinoline (139233-51-5)

Guidance literature:

Multi-step reaction with 7 steps

1: triethylamine / CH₂Cl₂ / 1 h / 3 °C

2: 43.0 g / BH₃*THF / tetrahydrofuran / 1.5 h / Heating

3: 6 N HCl / 2 h / 60 °C

4: 1.) dibenzoyl tartaric acid 2.) 1 N sodium hydroxide / 1.) ethanol, room temp.

5: CH₂Cl₂ / Ambient temperature

6: BBr₃ / CH₂Cl₂ / Ambient temperature

7: 3 N HCl / Heating

With hydrogenchloride; sodium hydroxide; borane-THF; rac-tartaric acid dibenzoate; boron tribromide; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1248/cpb.39.2910

Reference yield:

3-methoxy-2-methylbenzoic acid (55289-06-0) → (R)-(-)-4-(3,4-dihydroxyphenyl)-7-hydroxy-8-methyl-1,2,3,4-tetrahydroisoquinoline (139233-51-5)

Guidance literature:

Multi-step reaction with 8 steps

1: thionyl chloride / 0.67 h / Heating

2: triethylamine / CH₂Cl₂ / 1 h / 3 °C

3: 43.0 g / BH₃*THF / tetrahydrofuran / 1.5 h / Heating

4: 6 N HCl / 2 h / 60 °C

5: 1.) dibenzoyl tartaric acid 2.) 1 N sodium hydroxide / 1.) ethanol, room temp.

6: CH₂Cl₂ / Ambient temperature

7: BBr₃ / CH₂Cl₂ / Ambient temperature

8: 3 N HCl / Heating

With hydrogenchloride; sodium hydroxide; thionyl chloride; borane-THF; rac-tartaric acid dibenzoate; boron tribromide; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1248/cpb.39.2910

Reference yield:

N-[2-(3,4-Dimethoxy-phenyl)-2-hydroxy-ethyl]-3-methoxy-2-methyl-benzamide (119086-32-7) → (R)-(-)-4-(3,4-dihydroxyphenyl)-7-hydroxy-8-methyl-1,2,3,4-tetrahydroisoquinoline (139233-51-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 43.0 g / BH₃*THF / tetrahydrofuran / 1.5 h / Heating

2: 6 N HCl / 2 h / 60 °C

3: 1.) dibenzoyl tartaric acid 2.) 1 N sodium hydroxide / 1.) ethanol, room temp.

4: CH₂Cl₂ / Ambient temperature

5: BBr₃ / CH₂Cl₂ / Ambient temperature

6: 3 N HCl / Heating

With hydrogenchloride; sodium hydroxide; borane-THF; rac-tartaric acid dibenzoate; boron tribromide; In tetrahydrofuran; dichloromethane;

DOI:10.1248/cpb.39.2910

upstream raw materials:

3-methoxy-2-methylbenzoyl chloride

3-methoxy-2-methylbenzoic acid

N-[2-(3,4-Dimethoxy-phenyl)-2-hydroxy-ethyl]-3-methoxy-2-methyl-benzamide

1-(3,4-Dimethoxy-phenyl)-2-(3-methoxy-2-methyl-benzylamino)-ethanol