Ethyl 6-formylamino-5-methoxyindole-2-carboxylate

Base Information

• Chemical Name: Ethyl 6-formylamino-5-methoxyindole-2-carboxylate
• CAS No.: 119825-27-3
• Molecular Formula: C13H14N2O4
• Molecular Weight: 262.265
• DSSTox Substance ID: DTXSID40447359
• Wikidata: Q82266221
• Mol file: 119825-27-3.mol

Synonyms:119825-27-3;ETHYL 6-FORMYLAMINO-5-METHOXYINDOLE-2-CARBOXYLATE;Ethyl 6-formamido-5-methoxy-1H-indole-2-carboxylate;ethyl 6-formylamino-5-methoxy-1H-indole-2-carboxylate;SCHEMBL5257988;DTXSID40447359;BXQGUJOZARLMQY-UHFFFAOYSA-N;FT-0668279;J-004204

Chemical Property of Ethyl 6-formylamino-5-methoxyindole-2-carboxylate

Chemical Property:

• PSA: 83.91000
• LogP: 2.57100
• Storage Temp.: Refrigerator
• Solubility.: Ethanol, Methanol
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 262.09535693
• Heavy Atom Count: 19
• Complexity: 337

Purity/Quality:

97% ^*data from raw suppliers

Ethyl6-Formylamino-5-methoxyindole-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CC2=CC(=C(C=C2N1)NC=O)OC
• Uses: Ethyl 6-Formylamino-5-methoxyindole-2-carboxylate (cas# 119825-27-3) is a compound useful in organic synthesis.

Technology Process of Ethyl 6-formylamino-5-methoxyindole-2-carboxylate

There total 6 articles about Ethyl 6-formylamino-5-methoxyindole-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: 75.2%

ethyl pyruvate 3-formamido-4-methoxyphenyl-hydrazone (107575-59-7) → 6-(Formylamino)-5-methoxyindol-2-carbonsaeure-ethylester (119825-27-3)

Guidance literature:

With formic acid; at 80 ℃;

Reference yield: 3.0%

2-<<3-(Formylamino)-4-methoxyphenyl>hydrazono>propansaeure-ethylester → 6-(Formylamino)-5-methoxyindol-2-carbonsaeure-ethylester (119825-27-3) + 4-(Formylamino)-5-methoxyindol-2-carbonsaeure-ethylester

Guidance literature:

With formic acid; at 80 ℃; for 14h;

DOI:10.1002/hlca.19930760423

Reference yield:

3-amino-4-methoxynitrobenzene (99-59-2) → 6-(Formylamino)-5-methoxyindol-2-carbonsaeure-ethylester (119825-27-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1-(3-sulfopropyl)pyridinium phosphotungstate / 0.08 h / 70 °C

2.1: sodium tetrahydroborate / N,N-dimethyl-formamide / 120 h / 70 °C

3.1: hydrogenchloride / water / 0.5 h / -20 °C

3.2: 0.83 h / -15 °C

4.1: formic acid / 14 h / 80 °C

With hydrogenchloride; sodium tetrahydroborate; formic acid; 1-(3-sulfopropyl)pyridinium phosphotungstate; In water; N,N-dimethyl-formamide;

upstream raw materials:

C₁₃H₁₄⁽²⁾H₃N₃O₄

ethyl pyruvate 3-formamido-4-methoxyphenyl-hydrazone

3-amino-4-methoxynitrobenzene

N-(2-methoxyl-5-nitrophenyl)formamide

Downstream raw materials:

5-Methoxy-1H-pyrrolo<2,3-f>chinolin-2,7,9-tricarbonsaeure-(2-ethyl)(7,9-dimethyl)ester

4,5-Dihydro-4,5-dioxo-1H-pyrrolo<2,3-f>chinolin-2,7,9-tricarbonsaeure-(2-ethyl)(7,9-dimethyl)ester

pyrroloquinoline quinone

6-amino-5-methoxy-2-ethoxycarbonylindole

Refernces

• 1、 -. "SYNTHESIS OF PYRROLOQUINOLINE QUINONE (PQQ)". Page/Page column 9; 14; 1/6. . Retrieved 2010/11/24.
• 2、 Jongejan, Jaap A.,Bezemer, Roland P.,Duine, Johannis A.. "SYNTHESIS OF (13)C- AND (2)H-LABELLED PQQ". . p. 3709 - 3712. Retrieved 2007/10/02.