| Identification | Back Directory | [Name]
6-Bromo-3,4-dihydro-1H-[1,8]naphthyridin-2-one | [CAS]
129686-16-4 | [Synonyms]
4-dihydro-1H-[1
8]naphthyridin-2-one
6-Bromo-3,4-dihydro-1H-1,8phthyridin-2-one
6-Bromo-3,4-dihydro-1H-[1,8]naphthyrid-2-one
6-bromo-4,8-dihydro-3H-1,8-naphthyridin-2-one
6-Bromo-3,4-dihydro-1,8-naphthyridin-2(1H)-on
6-BROMO-3,4-DIHYDRO-1H-[1,8]NAPHTHYRIDIN-2-ONE
6-BROMO-3,4-DIHYDRO-1,8-NAPHTHYRIDIN-2(1H)-ONE
6-bioMo-3,4-dihydro-1H-[1,8]naphthyridin-2-one
6-bromo-3,4-dihydro-1,8-naphthyridin-2(8H)-one
1,8-Naphthyridin-2(1H)-one,6-broMo-3,4-dihydro-
6-bromo-3,4-dihydro-1h - [1,8] naphthidine-2-one
6-broMo-1,2,3,4-tetrahydro-1,8-naphthyridin-2-one
6-Bromo-2-oxo-1,2,3,4-tetrahydro-1,8-naphthyridine | [EINECS(EC#)]
251-156-6 | [Molecular Formula]
C8H7BrN2O | [MDL Number]
MFCD05664027 | [MOL File]
129686-16-4.mol | [Molecular Weight]
227.06 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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 |
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