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

Melting point:

214.8-215.0°C

storage temp. 

Sealed in dry,Room Temperature

form 

solid

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2932209090

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

Synthesis

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).

References

[1] Patent: WO2010/97410, 2010, A1. Location in patent: Page/Page column 121
[2] Patent: US2012/40942, 2012, A1. Location in patent: Page/Page column 56
[3] Journal of Medicinal Chemistry, 2009, vol. 52, # 12, p. 3644 - 3651
[4] Archiv der Pharmazie, 2015, vol. 348, # 1, p. 34 - 45
[5] Chemical Biology and Drug Design, 2014, vol. 84, # 6, p. 721 - 731

2-OXO-1,2-DIHYDRO-[1,8]NAPHTHYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER(5174-90-3)Related Product Information

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