6-Bromo-3,4-dihydro-1H-[1,8]naphthyridin-2-one Chemical Properties

Melting point:

265-267°C

Boiling point:

300.9±52.0 °C(Predicted)

Density 

1.83±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO

form 

Solid

pka

2.69±0.20(Predicted)

color 

Off- White to Yellow

InChI

InChI=1S/C8H7BrN2O/c9-6-3-5-1-2-7(12)11-8(5)10-4-6/h3-4H,1-2H2,(H,10,11,12)

InChIKey

VJEOGGNIBLORIJ-UHFFFAOYSA-N

SMILES

N1C2C(=CC(Br)=CN=2)CCC1=O

Safety Information

HS Code 

2933998090

6-Bromo-3,4-dihydro-1H-[1,8]naphthyridin-2-one Usage And Synthesis

Chemical Properties

Off- White to Yellow Solid

Synthesis

General procedure for the synthesis of 6-bromo-3,4-dihydro-1H-[1,8]naphthyridin-2-one from methyl 6-bromo-2-oxo-1,2,3,4-tetrahydro-1,8-naphthyridine-3-carboxylate: (c) 6-Bromo-3,4-dihydro-1H-1,8-naphthyridin-2-one (2.00 g, 7.0 mmol) was dissolved in CH3OH (75 mL) and 1.0 M NaOH solution (30 mL) was added. The reaction mixture was heated to reflux for 4 hours and subsequently cooled to room temperature. The reaction solution was neutralized with 1.0 M HCl (30 mL) and heated to reflux again overnight. The reaction slurry was concentrated to dryness and the residue was suspended with 95:5 CHCl3/CH3OH. The insoluble material was removed by filtration and the filtrate was concentrated to afford 6-bromo-3,4-dihydro-1H-[1,8]naphthyridin-2-one (1.40 g, 88% yield) as an off-white solid: mass spectra (electrospray ionization) m/e 228 (M + H)+.

References

[1] Patent: EP1226138, 2004, B1
[2] Patent: WO2011/61214, 2011, A1. Location in patent: Page/Page column 32
[3] Patent: WO2014/193647, 2014, A2. Location in patent: Paragraph 0288
[4] Patent: CN104119331, 2018, B. Location in patent: Paragraph 0836; 0851; 0852
[5] Journal of Medicinal Chemistry, 2003, vol. 46, # 9, p. 1627 - 1635

6-Bromo-3,4-dihydro-1H-[1,8]naphthyridin-2-one(129686-16-4)Related Product Information

• 6-Bromo-3,4-dihydro-2H-benzo[1,4]oxazine hydrochloride
• 6-BROMO-3,4-DIHYDRO-2H-PYRIDO[3,2-B][1,4]OXAZINE
• 6-BROMO-2H-PYRIDO[3,2-B][1,4]OXAZIN-3(4H)-ONE
• 6-BroMo-3-Methyl-2-pyridinaMine
• 2-Bromonaphthalene
• Nalidixic acid
• Malaridine
• Bromine
• 3,4-Dihydro-1,8-naphthyridin-2(1H)-one
• METHYL 6-BROMO-2-OXO-1,2,3,4-TETRAHYDRO-1,8-NAPHTHYRIDINE-3-CARBOXYLATE
• 2-Amino-5-bromo-3-methylpyridine
• 2-Acetylamino-5-bromo-3-methylpyridine
• 8-Bromo-3,4-dihydro-1H-[1,6]naphthyridin-2-one
• 1,2,3,4-TETRAHYDRO-1,8-NAPHTHYRIDINE
• Pyridine, 3-bromo-5-ethyl- (9CI)
• 5,6,7,8-Tetrahydro-[1,8]naphthyridine-3-bromide
• 6-Bromo-3,4-dihydro-1H-[1,8]naphthyridin-2-one
• 6-BROMO-2-OXO-1,2,3,4-TETRAHYDRO-1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID