454713-45-2

Usage

Uses

Used in Pharmaceutical Industry:
N-Boc-2-naphthylamine is used as a key intermediate in the synthesis of biphenyl-carbamate, the most active analog of Rhazinilam, an antitumor agent. N-Boc-2-naphthylamine plays a crucial role in the development of new and effective cancer treatments, as it contributes to the formation of potent antitumor drugs.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 91-59-8 naphthalen-2-ylamine 
• 75-65-0 tert-butyl alcohol 
• 93-09-4 naphthalene-2-carboxylate 
• 454713-47-4 tert-butyl (1-bromonaphthalen-2-yl)carbamate 
• 78191-00-1 N-Methoxy-N-methylacetamide 
• 79-30-1 isobutyryl chloride 
• 108-24-7 acetic anhydride 

Downstream Products

• 612-52-2 2-naphthylamine hydrochloride 
• 73190-70-2 N-(naphthalen-2-yl)-2-phenylacetamide 
• 17931-24-7 naphtho[2,1-d]thiazol-2(3H)-one 
• 20191-75-7 1-bromo-2-naphthylamine 
• 454713-41-8 tert-butyl 1-(chloromethyl)-1,2-dihydro-3H-benzo[e]indole-3-carboxylate 
• 7066-24-2 4H-benzo[f]quinazoline-1,3-dione 
• 7066-19-5 benzo[f]quinazolin-1(2H)-one 
• 91-20-3 naphthalene 
• 116632-14-5 2-amino-3-iodonaphthalene 
• 90016-93-6 2-Amino-1-iodonaphthalene 
• 1190098-20-4 1-(4-(methylsulfonyl)benzyl)-N-(naphthalen-2-yl)-1H-indazole-3-carboxamide 
• 454713-47-4 tert-butyl (1-bromonaphthalen-2-yl)carbamate 

Relevant academic research and scientific papers

Ultrasound promoted environmentally benign, highly efficient, and chemoselective N-tert-butyloxycarbonylation of amines by reusable sulfated polyborate

The sulfated polyborate catalyzed an efficient and chemoselective N-tert-butyloxycarbonylation of amines under ultrasonic irradiation is developed. A broad substrate scope has been demonstrated for N-Boc protection of various primary/secondary amines. It allows converting several aliphatic/aryl/heteroaryl amines, amino alcohol, aminoester, and chiral amines to their N-Boc-protected derivatives under solvent-free conditions with excellent yields. The protocol has several advantages such as easy catalyst, and product isolation, short reaction time, excellent yields, outstanding chemoselectivity, and catalyst recyclability, among others. This makes the process practicable, economical, and environmentally benign.

Sulfated tungstate: A highly efficient, recyclable and ecofriendly catalyst for chemoselective N-tert butyloxycarbonylation of amines under the solvent-free conditions

Sulfated tungstate catalyzed an efficient and ecofriendly protocol has been described for the chemoselective N-tert-butyloxycarbonylation of amines under the solvent-free conditions at room temperature. The variety of functionalized aliphatic, aromatic and heteroaromatic amines efficiently undergoes the N-tert-butyloxycarbonylation under the developed protocol. The aminoalcohol, aminophenol, aminoester as well as various chiral amines underwent the chemoselective N-Boc protection under the optimized reaction condition. The rapid reaction rate, mild conditions, very good functional group tolerance, excellent yield, solvent-free, easy recovery products and excellent catalyst recyclability are the advantages of this protocol. This makes the protocol feasible, economical and environmentally benign.

Nanoceria as an efficient and green catalyst for the chemoselective N-tert-butyloxycarbonylation of amines under the solvent-free conditions

Nanocerium oxide mediated an efficient and green protocol has been described for the chemoselective N-tert-butyloxycarbonylation of amines under the solvent-free conditions at ambient temperature. Various aliphatic, aromatic and heteroaromatic amines were protected using developed protocol and several functional groups such as alcohol, phenol and ester were well tolerated under these conditions. The rapid reaction rate, mild conditions, very good functional group tolerance, excellent yield, solvent-free, easy recovery products and excellent catalyst recyclability are the advantages of this protocol. This makes the protocol feasible, economical and environmentally benign.

Optimised synthesis of a nitroCBI hypoxia-activated prodrug with substantial anticancer activity

An optimised synthesis of a hypoxia-activated anticancer prodrug related to the duocarmycin family of natural products is described. The improved 10-step synthesis increases the overall yield from 4.4% to over 40% while requiring just 2 chromatography-bas

Synthesis of acylnaphthylamines and their applications in the formation of benzoquinazolines

The synthesis of acyl N-Boc-1- And N-Boc-2-naphthylamines and their transformation into alkyl substituted benzoquinazolines and benzoquinazolinones through the reaction with formamide or potassium cyanate in the presence of ammonium acetate is described.

Chemoselective: N-tert -butyloxycarbonylation of amines in glycerol

A catalyst-free, efficient and green protocol has been developed for the chemoselective N-Boc protection of amines by using glycerol as a solvent at room temperature. A variety of functionalized amines, such as aliphatic, aromatic as well as heteroaromatic were protected using the developed protocol. N-tert-Butyloxycarbonylation derivatives were formed without the formation of isocyanate, urea, N,N-di-t-Boc, or oxazolidinone as side products. The operational simplicity, cleaner reaction, rapid reaction convergence, functional group tolerance, excellent yield, high selectivity, catalyst-free feature and solvent recyclability are the distinct advantages of this protocol. Owing to these merits, this protocol is feasible, economical and environmentally benign.

6-bromo-2-aminonaphthalene preparation method

The invention provides a 6-bromo-2-aminonaphthalene preparation method. According to the present invention, the easily-available and inexpensive starting materials such as 2-aminonaphthalene, bromine,di-tert-butyl dicarbonate and the like are used; most of the intermediates are not required to be purified and directly enter the next step so as to substantially improve the consistency of the process; the high temperature and high pressure special reaction is not used so as to reduce the production risks; the yields of each reaction are high while the quality of the product meets the requirement; the amount of the three-waste is low so as to reduce the environmental protection pressure of the factory and meet the national conditions; and the product is refined by using the slat forming method so as to substantially improve the purity of the product.

Ligand-Promoted Meta-C-H Arylation of Anilines, Phenols, and Heterocycles

Here we report the development of a versatile 3-acetylamino-2-hydroxypyridine class of ligands that promote meta-C-H arylation of anilines, heterocyclic aromatic amines, phenols, and 2-benzyl heterocycles using norbornene as a transient mediator. More than 120 examples are presented, demonstrating this ligand scaffold enables a wide substrate and coupling partner scope. Meta-C-H arylation with heterocyclic aryl iodides as coupling partners is also realized for the first time using this ligand. The utility for this transformation for drug discovery is showcased by allowing the meta-C-H arylation of a lenalidomide derivative. The first steps toward a silver-free protocol for this reaction are also demonstrated.

Highly ortho-Selective Chlorination of Anilines Using a Secondary Ammonium Salt Organocatalyst

An organocatalytic, highly facile, efficient, and regioselective ortho-chlorination of anilines is described. A secondary ammonium chloride salt has been employed as the catalyst and the reaction can be conducted at room temperature without protection from air and moisture. In addition, the reaction is readily scalable and the catalyst can be recycled and reused. This catalytic protocol has been applied to the efficient synthesis of a highly potent c-Met kinase inhibitor. Mechanistic studies revealed that unique structural features of the secondary ammonium chloride salt are important for both the catalysis and regioselectivity of the electrophilic ortho-chlorination.

Palladium-catalyzed oxidative carbonylation of aromatic C-H bonds of N -alkylanilines with CO and alcohols for the synthesis of o -aminobenzoates

A Pd(II)-catalyzed C-H monocarbonylation of N-alkylanilines for the synthesis of o-aminobenzoates has been developed. Various aliphatic alcohols and phenol were tolerated in the reaction to afford the corresponding o-aminobenzoates in good yields under mild balloon pressure of CO.