INDOLE-3-(N,N-DIMETHYL)ACETAMIDE

Base Information

• Chemical Name: INDOLE-3-(N,N-DIMETHYL)ACETAMIDE
• CAS No.: 91566-04-0
• Molecular Formula: C12H14N2O
• Molecular Weight: 202.256
• Mol file: 91566-04-0.mol

Synonyms:HMS1424E14;Indol-3-yl-essigsaeure-dimethylamid;indol-3-yl-acetic acid dimethylamide;N,N-dimethylindole-3-acetamide;

Chemical Property of INDOLE-3-(N,N-DIMETHYL)ACETAMIDE

Chemical Property:

• Melting Point: 115-117°C
• PSA: 36.10000
• LogP: 1.79860
• Storage Temp.: Refrigerator
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly)

Purity/Quality:

98% ^*data from raw suppliers

N,N-Dimethyl-indole-3-acetamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N,N-Dimethyltryptamine intermediate. N,N-Dimethyltryptamine

Technology Process of INDOLE-3-(N,N-DIMETHYL)ACETAMIDE

There total 5 articles about INDOLE-3-(N,N-DIMETHYL)ACETAMIDE 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: 84.0%

indole (120-72-9) + N,N-dimethyl-1-hydroxyindole-3-acetamide → 2-(1H-indol-3-yl)-N,N-dimethylacetamide (91566-04-0) + 2,3-dihydro-1H,1'H-[2,3']biindolyl (6637-10-1) + 2-(2,2-di(1H-indol-3-yl)ethyl)aniline (6941-73-7) + N,N-dimethyl-1-(indol-3-yl)indole-3-acetamide (343604-87-5)

Guidance literature:

With formic acid; at 20 ℃; for 2h; Further byproducts given;

DOI:10.3987/COM-00-9135

Reference yield: 3.2%

N,N-dimethylamide-2'-chlorofumaranilide (105703-67-1) → 2-(1H-indol-3-yl)-N,N-dimethylacetamide (91566-04-0) + N,N-dimethyl-2-(oxindol-3-yl)acetamide (105643-23-0) + N,N-dimethyl-2'-ethylfumaranilide (105703-62-6)

Guidance literature:

With triethylaluminum; bis(acetylacetonate)nickel(II); triphenylphosphine; In toluene; at 60 - 80 ℃; for 5h;

Reference yield:

N,N-dimethylamide-2'-chlorofumaranilide (105703-67-1) → 2-(1H-indol-3-yl)-N,N-dimethylacetamide (91566-04-0) + N,N-dimethyl-2-(oxindol-3-yl)acetamide (105643-23-0) + 4-(N,N-dimethylcarbamoyl)-2-oxo-1,2,3,4-tetrahydroquinoline (105703-63-7) + N,N-dimethyl-2'-ethylfumaranilide (105703-62-6)

Guidance literature:

With tetrakis(triphenylphosphine)nickel⁽⁰⁾; triethylaluminum; In tetrahydrofuran; toluene; at 80 ℃; for 5h; Further byproducts given. Title compound not separated from byproducts;

upstream raw materials:

triethylaluminum

N,N-dimethylamide-2'-chlorofumaranilide

indole

Downstream raw materials:

2-(3-indole)-ethanol

N,N-dimethyltryptamine

Refernces

• 1、 Somei, Masanori,Yamada, Fumio,Hayashi, Toshikatsu,Goto, Aya,Saga, Yoshitomo. "Nucleophilic substitution reaction on the nitrogen of indole nucleus: Formation of 1-(indol-3-yl)indoles upon reaction of 1-hydroxyindoles with indole in formic acid". . p. 457 - 460. Retrieved 2007/10/03.
• 2、 Canoira, L.,Rodriguez, J. G.. "Synthesis of Oxindole Derivatives from N-Alkenyl-o-Chloroanilides with Zero-Valent Nickel Complex". . p. 1511 - 1518. Retrieved 2007/10/02.