2,3-Dioxoindoline-5-carboxamide

Base Information

• Chemical Name: 2,3-Dioxoindoline-5-carboxamide
• CAS No.: 28283-98-9
• Molecular Formula: C₉H₆N₂O₃
• Molecular Weight: 190.158
• Hs Code.: 2933990090
• ChEMBL ID: CHEMBL210381
• DSSTox Substance ID: DTXSID90469581
• Wikidata: Q82297365
• Mol file: 28283-98-9.mol

Synonyms:2,3-DIOXOINDOLINE-5-CARBOXAMIDE;28283-98-9;2,3-dioxo-1H-indole-5-carboxamide;MFCD09038153;isatin-5-carboxamide;CHEMBL210381;SCHEMBL5893915;DTXSID90469581;2, 3-dioxo-1H-indole-5-carboxamide;AKOS006240482;SB65841;SY273844;CS-0187979;P16941

Chemical Property of 2,3-Dioxoindoline-5-carboxamide

Chemical Property:

• PSA: 89.26000
• LogP: 0.75860
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 190.03784206
• Heavy Atom Count: 14
• Complexity: 313

Purity/Quality:

99% ^*data from raw suppliers

2,3-DIOXOINDOLINE-5-CARBOXAMIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1C(=O)N)C(=O)C(=O)N2

Technology Process of 2,3-Dioxoindoline-5-carboxamide

There total 6 articles about 2,3-Dioxoindoline-5-carboxamide 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: 1.0%

4-(α-Oximino-acetamino)-benzamid (17122-80-4) → 2,3-dioxo-5-indolinecarboxamide (28283-98-9)

Guidance literature:

With sulfuric acid; at 70 - 90 ℃; for 0.5h;

DOI:10.1016/j.ejmech.2020.112702

Reference yield:

2,3-dioxo-2,3-dihydro-1H-indole-5-carboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester → 2,3-dioxo-5-indolinecarboxamide (28283-98-9)

Guidance literature:

2,3-dioxo-2,3-dihydro-1H-indole-5-carboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester; With triethylamine; In 1,4-dioxane; at 20 ℃; for 24h;

With ammonia; In 1,4-dioxane; at 20 ℃; for 2h;

DOI:10.1021/jm0602357

Reference yield:

1H-indole-2,3-dione-5-carboxylic acid (25128-32-9) → 2,3-dioxo-5-indolinecarboxamide (28283-98-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: EDC / dimethylformamide / 4 h / 20 °C

2.1: Et₃N / dioxane / 24 h / 20 °C

2.2: NH₃ / dioxane / 2 h / 20 °C

With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1021/jm0602357

upstream raw materials:

1H-indole-2,3-dione-5-carboxylic acid

N-(4-ethoxycarbonylphenyl)-2-(hydroxyimino)acetamide

p-aminoethylbenzoate

4-aminobenzamide

Downstream raw materials:

3-[(4-Methylsulfamoyl-phenyl)-hydrazono]-2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid amide