ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carboxylate

Base Information

• Chemical Name: ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carboxylate
• CAS No.: 7272-58-4
• Molecular Formula: C12H15NO3
• Molecular Weight: 221.2524
• European Community (EC) Number: 819-467-4
• DSSTox Substance ID: DTXSID90223024
• Nikkaji Number: J1.728.356A
• Wikidata: Q83101390
• Mol file: 7272-58-4.mol

Synonyms:7272-58-4;ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carboxylate;BRN 0477542;3-METHYL-4-OXO-4,5,6,7-TETRAHYDRO-1H-INDOLE-2-CARBOXYLIC ACID ETHYL ESTER;ethyl 3-methyl-4-oxo-1,5,6,7-tetrahydroindole-2-carboxylate;4,5,6,7-Tetrahydro-3-methyl-4-oxo-indole-2-carboxylic acid ethyl ester;INDOLE-2-CARBOXYLIC ACID, 4,5,6,7-TETRAHYDRO-3-METHYL-4-OXO-, ETHYL ESTER;5-22-06-00213 (Beilstein Handbook Reference);Oprea1_794518;F1754-0022;SCHEMBL7052350;DTXSID90223024;HMS1719F13;4,5,6,7-tetrahydro-3-methyl-4-oxo-indole-2-carboxylicaciethylester;STK246715;AKOS000118581;SB38474;WAY-636030;NCGC00229745-01;NCGC00229745-02;LS-82791;CS-0222081;FT-0724099;EN300-11026;VU0421338-2;AB01321707-02;SR-01000454975;SR-01000454975-1;ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydro-1H-indole;Z57032538;2-carbethoxy-3-methyl-4-keto-4,5,6,7-tetrahydroindole;ethyl3-methyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carboxylate

Chemical Property of ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carboxylate

Chemical Property:

• Vapor Pressure: 1.54E-07mmHg at 25°C
• Melting Point: 165-167 °C(Solv: ethanol (64-17-5))
• Boiling Point: 428.2°Cat760mmHg
• PKA: 14.45±0.20(Predicted)
• Flash Point: 212.8°C
• PSA: 59.16000
• Density: 1.217g/cm³
• LogP: 2.01880
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 221.10519334
• Heavy Atom Count: 16
• Complexity: 303

Purity/Quality:

≥95% ^*data from raw suppliers

Ethyl3-methyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(C2=C(N1)CCCC2=O)C

Technology Process of ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carboxylate

There total 6 articles about ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydro-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: 60.0%

diethyl oximinomalonate (6829-41-0) + 1,3-cylohexanedione (504-02-9) → ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carboxylate (7272-58-4)

Guidance literature:

With sodium acetate; acetic acid; zinc; In water; Reflux;

DOI:10.1016/j.bmc.2008.10.002

Reference yield: 50.0%

ethyl acetoacetate (141-97-9) + 1,3-cylohexanedione (504-02-9) → ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carboxylate (7272-58-4)

Guidance literature:

ethyl acetoacetate; With acetic acid; sodium nitrite; for 3h;

1,3-cylohexanedione; With sodium acetate; zinc; In acetic acid; for 1h;

DOI:10.1021/ja070254l

Reference yield: 47.0%

1,3-cylohexanedione (504-02-9) + ethyl 2-hydroxyimino-3-oxobutanoate (5408-04-8) → ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carboxylate (7272-58-4)

Guidance literature:

With sodium acetate; acetic acid; zinc; for 1h; Heating;

DOI:10.1021/jo00044a012

upstream raw materials:

1,3-cylohexanedione

ethyl 2-hydroxyimino-3-oxobutanoate

(E)-2-(3-Oxo-cyclohex-1-enylamino)-but-2-enoic acid ethyl ester

3-(dimethylamino)cyclohex-2-en-1-one

Downstream raw materials:

benzyl 4-(2-ethoxycarbonylethyl)-3-methyl-5-<(3-methyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-2-yl)methyl>-1H-pyrrole-2-carboxylate

3-Methyl-4-oxo-4,5,6,7-tetrahydro-indol-2-carbonsaeure

2-amino-8-carbethoxy-7,9-dimethyl-4-oxo-3,5,6,7-tetrahydropyrimido<6,5-c>indole

2,5-dicarbethoxy-1,3-dimethyl-4-oxo-4,5,6,7-tetrahydroindole

Refernces

• 1、 Elliott, Luke D.,Berry, Malcolm,Orr-Ewing, Andrew J.,Booker-Milburn, Kevin I.. "The intramolecular photometathesis of pyrroles". . p. 3078 - 3079. Retrieved 2007/10/03.
• 2、 Lash, Timothy D.,Bladel, Karla A.,Shiner, Craig M.,Zajeski, Donna L.,Balasubramaniam, Rajiv P.. "Porphyrins with Exocyclic Rings. 1. Chemistry of 4,5,6,7-Tetrahydro-1H-indoles: Synthesis of Acetoxy Derivatives, Dihydroindoles, and Novel Porphyrins with Four Exocyclic Rings". . p. 4809 - 4820. Retrieved 2007/10/02.