24255-28-5

Upstream product

• 5470-18-8 2-Chloro-3-nitropyridine 
• 121-44-8 triethylamine 
• 3710-84-7 N-ethyl-N-hydroxy-ethanamine 
• 109-89-7 diethylamine 
• 1480-87-1 2-fluoro-3-nitropyridine 
• 2530-26-9 3-nitropyridine 

Relevant academic research and scientific papers

Photoredox catalyzed dealkylative aromatic halogen substitution with tertiary amines

A reaction of aromatic halides bearing electron-withdrawing groups with tertiary amines in the presence of an iridium catalyst under blue light irradiation is described. Products of the aromatic substitution of the halide by the dialkylamino fragment are

A palladium nanoparticle-catalyzed aryl-amine coupling reaction: High performance of aryl and pyridyl chlorides as the coupling partner

Carbon nitride (CN)-supported nanosized palladium particles, Pd-CN, have been found to be an active catalyst system for the amination of aryl and pyridyl chloride moieties in the presence of dialkyl amine under mild reaction conditions. The recyclability study of the reaction shows the stable performance of the catalyst without a significant loss of catalytic activity for a couple of cycles.

The oxidative amination of 3-nitropyridines

3-Nitropyridine was reacted with ammonia or alkylamines and KMnO4 under several different conditions. Substitutions in the para position to the nitro group were obtained with high regioselectivity: with ammonia, 2-amino-5-nitropyridine (66%), w

Reaction of metal diethylnitroxides with pentafluoropyridine, pentafluorobenzene, octafluorotoluene and 2-chloro-3- or 5-nitropyridine

Treatment of the nitroxides Et2NO(1-) M(1+) (2a-c) (M = Na, Li, K) and (Et2NO(1-))2Ba(2+) (2d) with pentafluoropyridine (3) at room temperature ( 1 d) gave in all cases the compounds Py-NEt2 (8), Py-ONEt2 (9), Py-NHEt (10) and Py-O(1-)H2NEt2(1+) (11) (where Py = tetrafluoro-4-pyridyl) in the approximate ratio 1:30:30:35.The radical traps, 1,4-dinitrobenzene or galvinoxyl, retarded the reaction (5 d required for complete consumption of 3), but the same products were formed in a similar ratio and compounds 8-11 were also formed by decomposition of the amine oxide Py-N(1+)O(1-)Et2 (20) 8 (57percent); 8 + (CF3CO)2O/H2O2 -> 20 (81percent) as the monohydrate>.It is proposed that the products 8-11 arose mainly via an SRN1 mechanism involving single electron transfer (SET) from the nitroxide 2 to the substrate 3 leading to the radical anion (21) and hence the tetrafluoro-4-pyridyl radical (22) which reacted with 2 at nitrogen to afford the amine oxide 20.Major Meisenheimer rearrangement of 20 gave hydroxylamine 9, while minor rearrangement afforded the hydroxylamine Py-N(Et)OEt (23) which eliminated ethanol to yield the secondary amine 10.Competing deoxygenation of 20 gave the tertiary amine 8 and the salt 11 was formed via decomposition of 8 in light (or on heating) involving homolytic fission of the weak N-O bond.Treatment of 9 with the acids AHF or CF3SO3H resulted in exothermic reaction and gave compounds 8 (27percent, 11percent), 10 (16percent, 18percent) and 11 (13percent, 25percent) via competing protonation at oxygen and nitrogen.The corresponding reactions of nitroxide 2a with the substrates C6HF5 (4) and C6F5CF3 (5) aforded the salt 4-H-C6F4-O(1-)H2NEt2(1+) (12) (15percent) and a mixture of the compounds 4-CF3-C6F4-R , respectively, while treatment of 2a with 2-chloro-3-nitropyridine (6) and 2-chloro-5-nitropyridine (7) gave the tertiary amines 2-N,N-diethylamino-3-nitropyridine (16) (35percent) or 2-N,N-diethylamino-5-nitropyridine (18) (25percent) together with N-(2-chloro-3-pyridyl)-N-(3-nitro-2-pyridyl)amine (17) (13percent) or N-(2-chloro-5-pyridyl)-N-(5-nitro-2-pyridyl)amine (19) (27percent) via presumed SRN1 pathways. - Keywords: Metal diethylnitroxides; Pentafluoropyridine; Pentafluorobenzene; Octafluorotoluene; 2-chloro-3-nitropyridine; 2-chloro-5-nitropyridine

Acyclic Tertiary Amines as Nucleophiles in Substitution Reactions of Aromatic and Heteroaromatic Halides

Even acyclic tertiary amines such as triethylamine, tri-n-propylamine and tri-n-butylamine, which have been believed to be inert to aromatic and heteroaromatic halides, underwent SNAr reactions with aromatic and heteroaromatic halides to give the dialkylamino derivatives; in the case of monocyclic amines like N-methylpyrrolidine and N-methylpiperidine, the dealkylation being regioselective.

Reaction of sodium diethylnitroxide with fluorobenzenes, pentafluoropyridine and halogenopyridines

Treatment of pentafluoropyridine with sodium diethylnitroxide in diethyl ether gave tetrafluoropyridines 4-RC5F4N(R = ONEt2, NEt2, NHEt and O- H2 N +Et2); in the presence of p-di