940-11-4

Upstream product

• 544-16-1 n-Butyl nitrite 
• 701-56-4 4-methoxy-N,N-dimethylanilne 
• 7647-01-0 hydrogenchloride 
• 104-94-9 4-methoxy-aniline 
• 5961-59-1 N-methyl-N-(4-methoxyphenyl)amine 
• 110-46-3 isopentyl nitrite 

Downstream Products

• 35292-54-7 N-methyl-N-(p-methoxyphenyl)hydrazine 
• 5961-59-1 N-methyl-N-(4-methoxyphenyl)amine 
• 46479-70-3 (+/-)-5-methoxy-3a,8-dimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole 
• 2731-01-3 (±)-5-methoxy-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo-[2,3-b]indole 
• 17591-06-9 5-methoxy-1,2-dimethyl-1H-indole 
• 59908-54-2 <(5-methoxy-1-methyl)indol-2-yl>carboxylic acid 
• 110516-03-5 1,2-dimethyl-6-(toluene-4-sulfonyloxy)-3,4-dihydro-1H-benz[cd]indol-5-one 
• 76137-90-1 [Pd((C₆H₃OCH₃-4)N(NO)CH₃)Cl(PPh₃)2] 
• 1416897-52-3 (E)-methyl 3-(5-methoxy-2-(methyl(nitroso)amino)phenyl)acrylate 
• 1416897-78-3 (E)-methyl 3-(5-methoxy-2-(methylamino)phenyl)acrylate 
• 187679-62-5 6-Methoxy-1-methyl-2-oxo-1,2,3,4-tetrahydroquinoline 
• 127473-29-4 5-methoxy-1-methyl-2,3-diphenyl-1H-indole 
• 64648-52-8 5-methoxy-1,3-dimethyl-2-phenyl-1H-indole 
• 1065474-24-9 3-methoxy-6-(methylamino)benzonitrile 

Relevant academic research and scientific papers

Rhodium(iii)-catalyzed indole synthesis at room temperature using the transient oxidizing directing group strategy

Rh-catalyzed reactions of N-alkyl anilines with internal alkynes at room temperature have been developed using an in situ generated N-nitroso group as a transient oxidizing directing group. Due to mild reaction conditions, this method enabled synthesis of a broad range of N-alkyl indoles, including even two indole-based medicinal compounds. Our work disclosed the feasibility of the transient oxidizing directing group strategy in C-H functionalization reactions, which possesses the potential to enhance overall step-economy and impart new reactivity patterns to substrates.

Copper(II)-catalyzed oxidative N-nitrosation of secondary and tertiary amines with nitromethane under an oxygen atmosphere

The combination of a catalytic amount of Cu(OTf)2 and less than a stoichiometric amount of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) under an O2 atmosphere effectively promoted the N-nitrosation of both secondary aromatic/aliphatic amines and tertiary aromatic amines with nitromethane (CH3NO2) leading to the preparation of N-nitrosamine derivatives.

Novel nitrosation polymer in organic synthesis

The present invention relates to a novel nitrosation polymer of the formula in which X, Y, R1, R2 and R3 are as defined in claim 1. The invention also relates to a process for the preparation of the said polymer.

Transnitrosation by N-aryl-N-nitrosoureas; NO-carrying O-nitrosoisourea

Transfer of nitroso groups, so-called transnitrosation, from aromatic N-nitroso compounds such as N-nitrosoureas, N-nitrosamides and N-nitrosamines, to aromatic amines or ureas was observed under non-acidic conditions at room temperature. Sterically hindered 3,3-dibenzyl-1-(4-tolyl)-1-nitrosourea (1a) rapidly nitrosates indoline, N-alkylanilines or 3-methyl-1-(4-tolyl)urea to give their N-nitroso derivatives. In the case of N,N-dimethylanilines, nitrosative demethylation occurs to give N-methyl-N-nitrosanilines. The transnitrosation is accelerated by electron-releasing groups on the nitroso acceptors, N-alkylanilines. The transnitrosation mechanism is considered to be as follows: N-nitrosourea (1) thermally decomposes to nitric oxide and ureidyl radical followed by formation of an O-nitrosoisourea intermediate (10), which acts as an NO-carrying agent and nitrosates anilines or ureas.

N-Dealkylation-N-nitrosation of Tertiary Aromatic Amines by n-Butyl Nitrite

N,N-Dialkyl aromatic amines with a variety of ring substituents are N-dealkylated and N-nitrosated efficiently by n-butyl nitrite/ammonium chloride/water at reflux temperature.Ring nitrosation was never observed, but minor amounts of m- and p-nitro amines and/or nitrosamines were formed in some cases.Ring nitration is rather a reaction of the initial substrate than a process occurring on formed nitrosamines.The leaving propensities of the initial N-substituents to yield nitrosamines were in the order benzyl >> methyl >> alkyl.Key Words: Nitrosamines; N-Dealkylation; N-Nitrosation; C-Nitration; Alkyl nitrite.

AROMATIC TERTIARY AMINES AND n-BUTYL NITRITE

The reaction between alkyl nitrites, particularly n-butyl nitrite, and tertiary aromatic amines under a variety of experimental conditions promptly yielded products of N-dealkylation-N-nitrosation, ring nitration, ipso-substitution and, occasionally, combinations of these processes.Aminoethers were detected as final products and intermediates on the way to N-nitrosations.Reaction pathways are suggested for some of the observed behaviours on the basis of experimental evidences whereas other alternatives are discarded.