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

105-53-3

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

5174-90-3

General procedure for the synthesis of ethyl 2-oxo-1,2-dihydro-[1,8]naphthyridine-3-carboxylate from 2-amino-3-pyridinecarboxaldehyde and diethyl malonate: 2-amino-3-pyridinecarboxaldehyde (1.0 g, 8.19 mmol) was suspended in a screw-capped pressure tube containing diethyl malonate (6.2 mL, 41.0 mmol). The reaction tube was sealed by the addition of piperidine (1.6 mL, 16.4 mmol). The reaction mixture was heated to 120°C and the reaction was kept at a constant temperature for 3.0 hours. Upon completion of the reaction, the mixture was allowed to cool to room temperature. The precipitate formed was collected by filtration and washed with ether (Et2O) to afford ethyl 2-oxo-1,2-dihydro-[1,8]naphthyridine-3-carboxylate 1.62 g in 91% yield. The structure of the product was confirmed by 1H NMR (CD3OD): δ 8.64 (m, 1H), 8.62 (s, 1H), 8.22 (m, 1H), 7.32 (m, 1H), 4.38 (m, 2H), 1.40 (t, 3H).

7521-41-7 Synthesis

7521-41-7
342 suppliers
$6.00/1g

105-53-3
787 suppliers
$5.00/25g

5174-90-3
61 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