5-Nitro-1H-indole-3-carboxamide

Base Information

• Chemical Name: 5-Nitro-1H-indole-3-carboxamide
• CAS No.: 128200-32-8
• Molecular Formula: C9H7N3O3
• Molecular Weight: 205.17000
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID20569624
• Wikidata: Q82456802
• Mol file: 128200-32-8.mol

Synonyms:5-nitroindole-3-carboxamide

Chemical Property of 5-Nitro-1H-indole-3-carboxamide

Chemical Property:

• PSA: 105.69000
• LogP: 2.58240
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 205.04874109
• Heavy Atom Count: 15
• Complexity: 289

Purity/Quality:

95% ^*data from raw suppliers

5-Nitro-1H-indole-3-carboxamide 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC2=C(C=C1[N+](=O)[O-])C(=CN2)C(=O)N

Technology Process of 5-Nitro-1H-indole-3-carboxamide

There total 5 articles about 5-Nitro-1H-indole-3-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: 61.17%

5-nitro-1H-indole-3-carboxylic acid (6958-37-8) → 5-nitro-1H-indole-3-carboxamide (128200-32-8)

Guidance literature:

With ammonium chloride; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 16h;

Reference yield:

oxalyl dichloride (79-37-8) + 5-nitro-1H-indole-3-carboxylic acid (6958-37-8) → 5-nitro-1H-indole-3-carboxamide (128200-32-8)

Guidance literature:

In tetrahydrofuran; 1,2-dichloro-ethane;

Reference yield:

5-nitroindole (6146-52-7) → 5-nitro-1H-indole-3-carboxamide (128200-32-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) trifluoroacetic anhydride (TFAA), 2.) aq. NaOH / 1.) reflux, 24 h

2: oxalyl chloride / tetrahydrofuran / 24 h / Ambient temperature

3: NH₃ gas / 1,2-dichloro-ethane

With sodium hydroxide; oxalyl dichloride; ammonia; trifluoroacetic anhydride; In tetrahydrofuran; 1,2-dichloro-ethane;

DOI:10.1021/jm00084a007

upstream raw materials:

5-nitro-1H-indole-3-carbonyl chloride

5-nitroindole

5-nitro-1H-indole-3-carboxylic acid

oxalyl dichloride

Downstream raw materials:

5-nitro-1H-indole-3-carbonitrile

Refernces

• 1、 Swain,Baker,Kneen,Herbert,Moseley,Saunders,Seward,Stevenson,Beer,Stanton,Watling,Ball. "Novel 5-HT3 antagonists: Indol-3-ylspiro(azabicycloalkane-3,5'(4'H)- oxazoles)". . p. 1019 - 1031. Retrieved 2007/10/02.