3-Isoquinolinecarboxylic acid, 1,2,3,4-tetrahydro-6-hydroxy-, Methyl ester

Base Information

• Chemical Name: 3-Isoquinolinecarboxylic acid, 1,2,3,4-tetrahydro-6-hydroxy-, Methyl ester
• CAS No.: 152495-61-9
• Molecular Formula: C₁₁H₁₃NO₃
• Molecular Weight: 207.229
• Mol file: 152495-61-9.mol

Synonyms:3-Isoquinolinecarboxylic acid, 1,2,3,4-tetrahydro-6-hydroxy-, Methyl ester;methyl 1,2,3,4-tetrahydro-6-hydroxyisoquinoline-3-carboxylate

Chemical Property of 3-Isoquinolinecarboxylic acid, 1,2,3,4-tetrahydro-6-hydroxy-, Methyl ester

Chemical Property:

• Boiling Point: 367.0±42.0 °C(Predicted)
• PKA: 9.75±0.40(Predicted)
• PSA: 58.56000
• Density: 1.231±0.06 g/cm3(Predicted)
• LogP: 0.90830

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Isoquinolinecarboxylic acid, 1,2,3,4-tetrahydro-6-hydroxy-, Methyl ester

There total 2 articles about 3-Isoquinolinecarboxylic acid, 1,2,3,4-tetrahydro-6-hydroxy-, Methyl ester 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: 96.0%

methanol (67-56-1) + 6-hydroxy-1,2,3,4-tetrahydro-3-isoquinoline carboxylic acid (76824-99-2,134388-87-7) → methyl 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate (152495-61-9)

Guidance literature:

With sulfuric acid;

DOI:10.1039/c7ra13148h

Reference yield:

D/L-3-hydroxy-phenylalanine (775-06-4,29562-33-2) → methyl 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate (152495-61-9)

Guidance literature:

Multi-step reaction with 2 steps

2: HCl / Heating

With hydrogenchloride;

DOI:10.1021/jm00077a001

Reference yield:

methyl 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate (152495-61-9) → 2-(diphenylacetyl)-6-phenyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) diisopropylethylamine / 1.) glyme, 5 min, 2.) glyme, RT, overnight

2: 90 percent / pyridine / Ambient temperature

3: 45 percent / LiCl, (Ph₃P)4Pd / dioxane / 72 h / Heating

4: 1.0 N aq. NaOH / methanol; tetrahydrofuran / 4 h / Heating

With pyridine; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; 1,4-dioxane; methanol;

DOI:10.1021/jm00077a001

upstream raw materials:

methanol

6-hydroxy-1,2,3,4-tetrahydro-3-isoquinoline carboxylic acid

D/L-3-hydroxy-phenylalanine

Downstream raw materials:

methyl 2-(diphenylacetyl)-6-phenyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

methyl 2-(diphenylacetyl)-6-<(trifluoromethyl)sulfonyl>-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

methyl 6-hydroxyisoquinoline-3-carboxylate

C₁₂H₁₁NO₃