5342-95-0

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 70, p. 4230, 1948 DOI: 10.1021/ja01192a073

InChI:InChI=1/C16H19NO/c18-16-9-8-13-6-2-3-7-14(13)15(16)12-17-10-4-1-5-11-17/h2-3,6-9,18H,1,4-5,10-12H2/p+1

Upstream product

• 2494-10-2 1-piperidinomethanol 
• 135-19-3 β-naphthol 
• 110-89-4 piperidine 
• 708-06-5 2-hydroxynaphthalene-1-carbaldehyde 
• 67-56-1 methanol 
• 50-00-0 formaldehyd 
• 2834-92-6 1-amino-2-naphthol 
• 597-31-9 2,2-dimethyl-3-hydroxypropionaldehyde 
• 880-09-1 di(N-piperidinyl)methane 
• 3275-13-6 1-(ethoxymethyl)piperidine 

Downstream Products

• 703-48-0 (+/-)-1ξ-methyl-(4ar,8at)-octahydro-naphthalen-2-one 
• 56771-15-4 1-methyl-5,6,7,8-tetrahydro-2-naphthol 
• 86088-40-6 1-Methyl-1,2,3,4-tetrahydro-[2]naphthol 

Relevant academic research and scientific papers

Manganese-Catalyzed Aminomethylation of Aromatic Compounds with Methanol as a Sustainable C1 Building Block

This study represents the first example of a manganese-catalyzed environmentally benign, practical three-component aminomethylation of activated aromatic compounds including naphtols, phenols, pyridines, indoles, carbazoles, and thiophenes in combination with amines and MeOH as a C1 source. These reactions proceed with high atom efficiency via a sequence of dehydrogenation and condensation steps which give rise to selective C-C and C-N bond formations, thereby releasing hydrogen and water. A well-defined hydride Mn(I) PNP pincer complex, recently developed in our laboratory, catalyzes this process in a very efficient way, and a total of 28 different aminomethylated products were synthesized and isolated yields of up to 91%. In a preliminary study, a related Fe(II) PNP pincer complex was shown to catalyze the methylation of 2-naphtol rather than its aminomethylation displaying again the divergent behavior of isoelectronic Mn(I) and Fe(II) PNP pincer systems.

An amino-naphthol preparation method of compound

The invention relates to a preparation method for aminonaphthol compound. The method includes the following steps: catalyst, aldehyde compound, secondary amine compound and naphthol are sequentially added into water and react under the temperature condition of 20 DEG C to 80 DEG C, and after reaction is complete, reaction liquid is obtained; the reaction liquid is sequentially extracted, dried, concentrated and separated by column chromatography according to the conventional method, so that product I or product II is obtained, and the structural formula of the product is shown in the figure. The preparation method has the advantages of mild conditions, short reaction time, simple post-processing, high yield and environment-friendliness, can realize mass production and has a good industrial application prospect.

Divergent reaction: Metal & oxidant free direct C-H aryloxylation and hydride free formal reductive N-benzylation of N-heterocycles

Metal, oxidant and other additive-free novel methods for direct C-H aryloxylation of aliphatic amines are developed. In the presence of excess amine, the course of the reaction was diverted, producing various arylmethylamines via hydride-free formal reductive amination. Involvement of a quinone methide intermediate was revealed from mechanistic studies. This journal is

[Omim][Bf4] ionic liquid, a green and recyclable medium for one-pot aminomethylation of electron-rich aromatic compounds

An efficient catalyst-free procedure has been developed for one-pot aminomethylation of some electron-rich aromatic compounds such as 1- and 2-naphthols, indole, N-methylindol and benzamide, in [omim][BF4] ionic liquid at room temperature. The ionic liquid can be recovered and reused without any noticeable loss of performance.

Novel synthesis of 2,2-dialkyl-3-dialkylamino-2,3-dihydro-1H-naphtho[2,1-b]pyrans

2,2-Dialkyl-3-dialkylamino-2,3-dihydro-1H-naphtho[2,1-b]pyrans were prepared from 2-naphthol, a secondary amine, and 3-hydroxy-2,2-dialkylpropanal in the presence of a catalytic amount of p-toluenesulfonic acid. This one-pot reaction involves retro-aldol

Novel synthesis of 2-naphthol Mannich bases and their NMR behaviour

A novel two-step procedure involving the formation of 1-arylidene-2- tetralones from 2-tetralone and subsequent Michael addition of a cyclic secondary amine on the alkenone followed by in situ aerial oxidation was developed to produce 2-naphthol Mannich bases. A simple microwave-assisted one-pot synthesis of 2-naphthol Mannich bases was also carried out under solvent-free conditions from 2-naphthol and corresponding aldehydes and amines in the presence of p-toluenesulfonic acid. The compounds of this series displayed interesting NMR behaviour. Extensive variable-temperature NMR investigations, including HSQC experiments, are herein reported. NMR results on the conformation in solution phase were found to be consistent with the X-ray crystal structure in the solid state.

Intramolecular Interactions I. The Use of Some Mannich Bases of Naphthols as Model Compounds for Intramolecular Hydrogen Bonding

Some model compounds for intramolecular hydrogen bonding are presented.The nmr, IR, UV and fluorescence spectra are shown to be suited for the study of such hydrogen bonds. - Keywords: Hydrogen bond; Intramolecular proton transfer; Mannich bases