3-[2-(Dimethylamino)vinyl]-4-nitropyridine 1-Oxide

Base Information

• Chemical Name: 3-[2-(Dimethylamino)vinyl]-4-nitropyridine 1-Oxide
• CAS No.: 104118-88-9
• Molecular Formula: C9H11N3O3
• Molecular Weight: 209.205
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID90706741
• Mol file: 104118-88-9.mol

Synonyms:104118-88-9;3-[2-(Dimethylamino)vinyl]-4-nitropyridine 1-Oxide;Ethenamine, N,N-dimethyl-2-(4-nitro-1-oxido-3-pyridinyl)-;N,N-dimethyl-2-(4-nitro-1-oxidopyridin-1-ium-3-yl)ethenamine;DTXSID90706741;MFCD12405620;AKOS028109910;SB55468;SY024746;N,N-Dimethyl-2-(4-nitro-1-oxo-1lambda~5~-pyridin-3-yl)ethen-1-amine

Chemical Property of 3-[2-(Dimethylamino)vinyl]-4-nitropyridine 1-Oxide

Chemical Property:

• PSA: 74.52000
• LogP: 2.07880
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 209.08004122
• Heavy Atom Count: 15
• Complexity: 250

Purity/Quality:

99% ^*data from raw suppliers

3-[2-(Dimethylamino)vinyl]-4-nitropyridine1-Oxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C=CC1=C(C=C[N+](=C1)[O-])[N+](=O)[O-]

Technology Process of 3-[2-(Dimethylamino)vinyl]-4-nitropyridine 1-Oxide

There total 2 articles about 3-[2-(Dimethylamino)vinyl]-4-nitropyridine 1-Oxide 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: 98.0%

3-methyl-4-nitropyridine N-oxide (1074-98-2) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 3-dimethylaminovinylene-4-nitropyridine-l-oxide (104118-88-9)

Guidance literature:

In N,N-dimethyl-formamide; at 100 ℃; for 1.5h;

DOI:10.1021/jm301217c

Reference yield:

3-picoline-N-oxide (1003-73-2) → 3-dimethylaminovinylene-4-nitropyridine-l-oxide (104118-88-9)

Guidance literature:

Multi-step reaction with 2 steps

1: nitric acid; sulfuric acid / 3 h / 100 - 105 °C

2: N,N-dimethyl-formamide / 1.5 h / 100 °C

With sulfuric acid; nitric acid; In N,N-dimethyl-formamide;

DOI:10.1021/jm301217c

Reference yield: 74.5%

3-dimethylaminovinylene-4-nitropyridine-l-oxide (104118-88-9) → 5-azaindole (271-34-1)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; at 20 - 65 ℃; for 8h; under 1500.15 - 2250.23 Torr; Inert atmosphere; Autoclave;

DOI:10.1021/jm301217c

upstream raw materials:

3-methyl-4-nitropyridine N-oxide

N,N-dimethyl-formamide dimethyl acetal

3-picoline-N-oxide

Downstream raw materials:

4-nitro-3-pyridinecarbaldehyde 1-oxide

ethyl 2-(5-azaindol-3-yl)-2-oxoacetate

5-azaindole

Refernces

• 1、 Ganser, Christopher,Lauermann, Eva,Maderer, Annett,Stauder, Torsten,Kramb, Jan-Peter,Plutizki, Stanislav,Kindler, Thomas,Moehler, Markus,Dannhardt, Gerd. "Novel 3-azaindolyl-4-arylmaleimides exhibiting potent antiangiogenic efficacy, protein kinase inhibition, and antiproliferative activity". . p. 9531 - 9540. Retrieved 2013/01/16.