1H-Indole-3-acetic acid, 2-acetyl-

Base Information

• Chemical Name: 1H-Indole-3-acetic acid, 2-acetyl-
• CAS No.: 91569-49-2
• Molecular Formula: C12H11NO3
• Molecular Weight: 217.224
• DSSTox Substance ID: DTXSID90452615
• Wikidata: Q82273359
• Mol file: 91569-49-2.mol

Synonyms:1H-Indole-3-acetic acid, 2-acetyl-;91569-49-2;2-acetyl-3-indolylacetic acid;2-Acetyl-indole-3-acetic acid;DTXSID90452615

Chemical Property of 1H-Indole-3-acetic acid, 2-acetyl-

Chemical Property:

• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 217.07389321
• Heavy Atom Count: 16
• Complexity: 303

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)C1=C(C2=CC=CC=C2N1)CC(=O)O

Technology Process of 1H-Indole-3-acetic acid, 2-acetyl-

There total 2 articles about 1H-Indole-3-acetic acid, 2-acetyl- 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: 48.0%

indole-3-acetic acid (87-51-4) + acetic anhydride (108-24-7) → 1-methylpyrano[3,4-b]indol-3(9H)-one (35296-53-8) + (2-acetyl-3-indolyl)acetic acid (91569-49-2)

Guidance literature:

Mechanism; F₃B-OEt₂;

Reference yield: 28.0%

indole-3-acetic acid (87-51-4) → 1-methylpyrano[3,4-b]indol-3(9H)-one (35296-53-8) + (2-acetyl-3-indolyl)acetic acid (91569-49-2)

Guidance literature:

With boron trifluoride diethyl etherate;

Reference yield: 80.0%

(2-acetyl-3-indolyl)acetic acid (91569-49-2) → 2-acetyl-3-methylindole (16244-23-8)

Guidance literature:

In various solvent(s); at 156 ℃; for 96h;

upstream raw materials:

indole-3-acetic acid

acetic anhydride

Downstream raw materials:

1-methylpyrano[3,4-b]indol-3(9H)-one

2-acetyl-3-methylindole

C₁₈H₁₇N₃O₂

2-acetyl-N-[(R)-2-hydroxy-1-phenylethyl]-3-indoleacetamide

Refernces

Heterocyclization of 2-acyl-3-indolylacetic acids using hydrazine. Synthesis of 2,3-dihydro-2-oxo-5-R¹-1H-[1,2]diazepino[4,5-b]indoles

10.1007/s10593-009-0322-7

The research focuses on the heterocyclization of 2-acetyl-3-indolylacetic acids using hydrazine, with the aim of synthesizing 2,3-dihydro-2-oxo-5-R1-1H-[1,2]diazepino[4,5-b]indoles. The experiments involved various reactants, including 2-acetyl-3-indolylacetic acid derivatives, hydrazine hydrate, and different amines, leading to the formation of compounds such as 2-aminoindolo[2,3-c]pyridin-3(2H)-one and azines. The study also explored the synthesis of these diazepino[4,5-b]indoles through the reaction of 1-alkylaminoacetylindolo[2,3-c]pyrilium perchlorates and methyl esters of 2-acetyl- and 2-propionyl-3-indolylacetic acid with hydrazine hydrate. The analyses used to characterize the synthesized compounds included 1H NMR spectroscopy, mass spectrometry, and X-ray diffraction structural analysis, which provided detailed information on the chemical shifts, molecular structure, and crystallographic data of the compounds.