ChemicalBook CAS DataBase List 2-OXO-1,2-DIHYDRO-[1,8]NAPHTHYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER

2-OXO-1,2-DIHYDRO-[1,8]NAPHTHYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER synthesis

6synthesis methods

Product Name:2-OXO-1,2-DIHYDRO-[1,8]NAPHTHYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER
CAS Number:5174-90-3
Molecular formula:C11H10N2O3
Molecular Weight:218.21

7521-41-7 Synthesis

7521-41-7
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$6.00/1g

105-53-3
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2-OXO-1,2-DIHYDRO-[1,8]NAPHTHYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER

5174-90-3
52 suppliers
$24.00/250mg

Yield:5174-90-3 97%

Reaction Conditions:

with piperidine at 120;

Steps:

Ethyl2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate (38).

A solution of commercially available 2-aminonicotinaldehyde(1.00g, 8.19 mmol), diethyl malonate (1.85 ml, 12.18mmol) and few drops of piperidine was stirred at 120°C for 20 hours. After themixture was cooled, the precipitate formed during the reaction was treated withethyl ether and then dried to give a yellow solid (1.74 g, 7.96 mmol, 97%yield). H-NMR (CDCl₃): δ 1.42(t, 3H, J=7.2, CH₃); 4.44(q, 2H, J= 7.2, CH₂);7.27(dd, 1H, J=4.8 Hz, J=8 Hz, Ar); 8.04 (dd, 1H, J=1.6 Hz, J=8 Hz, Ar); 8.47(s, 1H, Ar); 8.90 (dd, 1H, J=1.6 Hz, J=4.8 Hz, Ar); 12.62 (s, 1H, NH) ppm.

References:

Sestito, Simona;Bacci, Andrea;Chiarugi, Sara;Runfola, Massimiliano;Gado, Francesca;Margheritis, Eleonora;Gul, Sheraz;Riveiro, Maria E.;Vazquez, Ramiro;Huguet, Samuel;Manera, Clementina;Rezai, Keyvan;Garau, Gianpiero;Rapposelli, Simona [European Journal of Medicinal Chemistry,2021,vol. 226,art. no. 113895] Location in patent:supporting information