19281-11-9

Usage

Uses

Used in Pharmaceutical Industry:
N,N-Diethyl-3-nitrobenzeneacetamide is used as an intermediate in the preparation of Ropinirole derivatives for the development of medications. Its role in the synthesis process is crucial for creating effective pharmaceutical compounds that can be utilized in various therapeutic applications.

Upstream product

• 1497283-51-8 C₁₂H₁₆N₂O₃ 
• 99-61-6 3-nitro-benzaldehyde 
• 444681-65-6 1,1-dibromo-2-(3-nitrophenyl)ethene 
• 109-89-7 diethylamine 
• 1877-73-2 3-nitro-benzeneacetic acid 
• 38411-41-5 (3-nitrophenyl)acetyl chloride 

Downstream Products

• 932405-32-8 N,N-diethyl-2-(3-nitrophenyl)ethanamine 
• 932394-03-1 3-(2-(diethylamino)ethyl)benzenamine 
• 58730-44-2 C₁₂H₁₈N₂O 

Relevant academic research and scientific papers

Amination of phenylketenes. Substituent effect on amine-catalyzed tautomerization of amide enol

The transient intermediates with infrared bands at 1676-1680 cm -1 observed for reaction of substituted phenylketenes with diethylamine in acetonitrile were suggested to be the amide enols rather than the zwitterions on the basis of the theoretical calculations. A single broad band at 1674 cm-1 observed for reaction with the primary amines was attributed to overlap of two bands of the intermediate (amide enol) and the final product (amide). The substituent effect for the second-order rate constants of diethylamine-catalyzed tautomerization of the amide enol intermediates to give the amides was analyzed successfully by the Yukawa-Tsuno equation, giving a ρ value of 0.63 and an r- value of 1.31. The r- value larger than unity for pKa of phenols indicates that the negative charge formed at an oxygen atom of the amide enol at the transition state is significantly delocalized into the aromatic π-system through the ethenyl group. This r- value was considered to reflect an intrinsic property of β-phenylenolate skeleton. A remarkably small ρ value attributes to the cyclic transition structure where the negative charge disperses in a six-member ring. Copyright 2013 John Wiley & Sons, Ltd. The substituent effect for the reaction of the amide enol intermediate generated from phenylketene with diethylamine has been analyzed. The large r- of 1.31 was attributed to an intrinsic property of β-phenylenolate skeleton. A remarkably small ρ of 0.63 suggested the cyclic transition structure. Copyright

Synthesis and biological evaluation of new 4β-anilino-4′-O- demethyl-4-desoxypodophyllotoxin derivatives as potential antitumor agents

A series of new 4β-anilino-4′-O-demethyl-4-desoxypodophyllotoxin derivatives were prepared and evaluated for their cytotoxicities against four human cancer cell lines including KB, KB/VCR, A549 and 95D. Most compounds showed better growth-inhibition activities against tested cell lines than that of etoposide (VP-16). Preliminary structure-activity relationships (SARs) were concluded and it indicated that the side chains substituted at 4β position of podophyllotoxin significantly influenced the cytotoxic activity, especially for the drug resistance profile. In vivo studies of compound 26c on highly metastatic human lung cancer xenograft in nude mice showed that it can significantly inhibit tumor growth with administrating by oral route.

On the Synthesis and Basicity of 1,3-Diaminoisoquinolines

A series of 6- and 7-substituted derivatives of 1,3-diaminoisoquinoline were synthesized by the reaction of N,N-diethylarylacetamides with POCl 3 and then with N,N-dimethylcyanamide. The products were identified by means of spectroscopic methods and their pKa dissociation constants were determined.