Ethyl 3-hydroxy-5-methoxy-1H-indole-2-carboxylate

Base Information

• Chemical Name: Ethyl 3-hydroxy-5-methoxy-1H-indole-2-carboxylate
• CAS No.: 318292-61-4
• Molecular Formula: C₁₂H₁₃NO₄
• Molecular Weight: 235.24
• Hs Code.: 2933990090
• Mol file: 318292-61-4.mol

Synonyms:Ethyl 3-hydroxy-5-methoxy-1H-indole-2-carboxylate;3-HYDROXY-5-METHOXY-1H-INDOLE-2-CARBOXYLIC ACID ETHYL ESTER;

Chemical Property of Ethyl 3-hydroxy-5-methoxy-1H-indole-2-carboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• PSA: 71.55000
• Density: 1.316
• LogP: 2.05880
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

Ethyl3-hydroxy-5-methoxy-1H-indole-2-carboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Ethyl 3-hydroxy-5-methoxy-1H-indole-2-carboxylate

There total 3 articles about Ethyl 3-hydroxy-5-methoxy-1H-indole-2-carboxylate 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: 88.0%

3-formyl-5-methoxy-indole-2-carboxylic acid ethyl ester (36820-78-7) → 3-hydroxy-5-methoxyindole-2-carboxylic acid ethyl ester (318292-61-4)

Guidance literature:

With toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 8h;

DOI:10.1039/c1cc11253h

Reference yield:

ethyl 5-methoxy-1H-indole-2-carboxylate (4792-58-9) → 3-hydroxy-5-methoxyindole-2-carboxylic acid ethyl ester (318292-61-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 85 percent / POCl₃ / 1,2-dichloro-ethane / Heating

2.1: m-CPBA; PTSA / CH₂Cl₂ / 10 °C

2.2: 79 percent / Me₂S; EtOH

With toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; trichlorophosphate; In dichloromethane; 1,2-dichloro-ethane; 1.1: Vilsmeier-Haack reaction / 2.1: Baeyer-Villiger oxidation;

DOI:10.1016/S0040-4039(00)01456-8

Reference yield:

5-methoxy-1H-indole-2-carboxylic acid (4382-54-1) → 3-hydroxy-5-methoxyindole-2-carboxylic acid ethyl ester (318292-61-4)

Guidance literature:

Multi-step reaction with 3 steps

1: sulfuric acid / Reflux

2: trichlorophosphate / 20 °C

3: toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 8 h / 20 °C

With sulfuric acid; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; trichlorophosphate; In dichloromethane; 2: Vilsmeier formylation / 3: Baeyer-Villiger oxidation;

DOI:10.1039/c1cc11253h

upstream raw materials:

3-formyl-5-methoxy-indole-2-carboxylic acid ethyl ester

ethyl 5-methoxy-1H-indole-2-carboxylate

5-methoxy-1H-indole-2-carboxylic acid

Downstream raw materials:

1-allyl-2-benzyl-5-methoxy-3-oxo-2,3-dihydro-1H-indole-2-carboxylic acid ethyl ester