125902-26-3

Basic information

• Product Name: Methyl 1,8-naphthyridine-2-carboxylate
• Synonyms: Methyl 1,8-naphthyridine-2-carboxylate;2-(Methoxycarbonyl)-1,8-naphthyridine
• CAS NO: 125902-26-3
• Molecular Formula: C10H8N2O2
• Molecular Weight: 188.18272
• Mol File: 125902-26-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Methyl 1,8-naphthyridine-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 1,8-naphthyridine-2-carboxylate(125902-26-3)
• EPA Substance Registry System: Methyl 1,8-naphthyridine-2-carboxylate(125902-26-3)

Safety Data

• Hazardous Substances Data: 125902-26-3(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 215523-34-5 1,8-naphthyridine-2-carboxylic acid 
• 125902-24-1 2-(Trichloromethyl)-1,8-naphthyridine 
• 7521-41-7 2-Aminonicotinaldehyde 
• 1569-16-0 2-methyl-[1,8]naphthyridine 

Downstream Products

• 125902-27-4 2-(Hydroxymethyl)-1,8-naphthyridine 
• 924279-01-6 methyl 5,6,7,8-tetrahydro-1,8-naphthyridine-2-carboxylate 
• 289677-07-2 Naphthyridineamide 

Relevant articles and documents

Iridium complexes with ligands of 1,8-Naphthyridine-2-carboxylic acid derivatives-preparation and catalysis

Complexation of 1,8-naphthyridine(Np)-2-carboxylic derivatives L1-L3 [L1 = Np-2-COOH, L2 = Np-2-CONH2, L3 = Np-2-CONHCH2Py] with [Ir(COD)(μ-OMe)]2 yielded the corresponding complexes [Ir(COD)(Ln)] (1~3, n = 1~3, respectively). The potential tridentate L3 behaves as a bidentate donor in the complex 3. Treatment of L1 with [Ir(COD)Cl]2 under nitrogen atmosphere gave a Ir(III) hydride complex [Ir(COD)(L1)HCl] (4). However, carrying out the reaction in the presence of oxygen rendered a Ir(III) dichloride species [Ir(COD)(L1)Cl2] (5). All these complexes were characterized by spectroscopic analyses and X-ray single crystal determination. Catalytic activity of iridium complexes in amination of amines with alcohols was screened. It appears that iridium amido complexes 2 and 3 show excellent catalytic activity on amination of anilines with alcohols in the presence of Cs2CO3 at 120 °C.

FUSED BICYCLIC HETEROCYCLE DERIVATIVES AS PESTICIDES

The invention relates to novel compounds of the formula (I) or (I′) in which R1, R2, R3, Aa, Ab, Ac, Ad, Ae, Q and n have the definitions given above, to the use thereof as acaricides and/or insecticides for controlling animal pests and to processes and intermediates for the preparation thereof.

ANTIBACTERIAL AGENTS

Naphthalene, quinoline, quinoxaline and naphthyridine derivatives useful in the treatment of bacterial infections in mammals, particularly humans, are disclosed herein.

Functionalization of 2-Methyl- and 2,7-Dimethyl-1,8-naphthyridine

A new synthesis of 2,7-dimethyl-1,8-naphthyridine (dmnap) from 2-methyl-1,8-naphthyridine (mnap) upon treatment with 3 equiv of methyllithium is described.Oxidation of dmnap with 8 equiv of N-chlorosuccinimide gave (98percent) 2,7-bis(trichloromethyl)-1,8-naphthyridine (2), while oxidation with 4 equiv gave (97percent) 2,7-bis(dichloromethyl)-1,8-naphthyridine (1).Hydrolysis of 2 phosphoric acid followed by esterification gave the corresponding diester 3 in 80percent overall yield.Reduction of 3 with NaBH(OMe)3 afforded (55percent) diol 4.Similar functionalization of mnap afforded 2-(trichloromethyl)-1,8-naphthyridine (6) in 85-94percent yield along with 6-chloro-2-(trichloromethyl)-1,8-naphthyridine (7).Methanolysis of 6 gave (78percent) 2-(methoxycarbonyl)-1,8-naphthyridine (8), which upon reduction with NaBH(OMe)3 afforded (59percent) the alcohol 9.Treatment of 6 with KOH caused a displacement of the trichloromethyl moiety, generating 1,8-naphthyridin-2-one (10) as the sole product.Similarly, 2 gave 7-(trichloromethyl)-1,8-naphthyridin-2-one (11) under mild conditions or 7-(ethoxycarbonyl)-1,8-naphthyridin-2-one (12) when refluxed.