Identification | Back Directory | [Name]
2-Pyridinecarboxylic acid, 1,6-dihydro-6-oxo-1-(phenylMethoxy)- | [CAS]
210366-15-7 | [Synonyms]
6-oxo-1-phenylmethoxypyridine-2-carboxylic acid 1-(benzyloxy)-2-oxo-1,2-dihydropyridine-6-carboxylic acid 1-(Benzyloxy)-6-oxo-1,6-dihydropyridine-2-carboxylic acid 1,6-dihydro-6-oxo-1-(phenylMethoxy)-2-Pyridinecarboxylic acid 2-Pyridinecarboxylic acid, 1,6-dihydro-6-oxo-1-(phenylMethoxy)- | [Molecular Formula]
C13H11NO4 | [MDL Number]
MFCD20270106 | [MOL File]
210366-15-7.mol | [Molecular Weight]
245.23 |
Chemical Properties | Back Directory | [Melting point ]
176-177 °C | [Boiling point ]
403.3±55.0 °C(Predicted) | [density ]
1.38±0.1 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [pka]
3.98±0.20(Predicted) | [Appearance]
Off-white to light yellow Solid |
Hazard Information | Back Directory | [Synthesis]
General procedure for the synthesis of 1-(benzyloxy)-6-oxo-1,6-dihydropyridine-2-carboxylic acid from benzyl chloride and 1-hydroxy-6-oxo-1,6-dihydropyridine-2-carboxylic acid: 1-hydroxy-6-carboxy-2(1H)-pyridinone (15.5 g, 0.1 mol) and anhydrous potassium carbonate (27.6 g, 0.2 mol) were mixed with benzyl chloride (15.2 g, 0.12 mol) were mixed in methanol (250 mL) and reacted at reflux for 16 hours. After completion of the reaction, the mixture was filtered and the filtrate was evaporated to dryness. The residue was dissolved in water (50 mL) and acidified with 6N HCl to pH 2. A white precipitate was isolated by filtration, washed with cold water, and dried under vacuum to give 22.3 g (91% yield) of 1-benzyloxy-6-carboxy-2(1H)-pyridinone with a melting point of 176-177 °C. The product was purified by 1H NMR (1H NMR) (1H NMR) and dried under vacuum. The product was characterized by 1H NMR (300 MHz, CDCl3) and 13C NMR (75 MHz, DMSO-d6) with the following data: 1H NMR δ 5.269 (s, 2H), 6.546 (dd, J = 16 Hz, J = 6.7 Hz, 1H), 6.726 (dd, J = 16 Hz, J = 9.2 Hz, 1H), 7.39 -7.51 (m, 6H); 13C NMR δ 77.9, 106.0, 124.1, 128.5, 129.1, 129.6, 133.8, 138.7, 140.5, 157.7, 161.7. Elemental analysis (C13H11NO4) calculated values: C, 63.66 (63.75); H, 4.53 (4.55) N, 5.71 (5.52). | [References]
[1] Journal of Medicinal Chemistry, 2014, vol. 57, # 11, p. 4849 - 4860 [2] Journal of Medicinal Chemistry, 2002, vol. 45, # 18, p. 3963 - 3971 [3] Patent: WO2008/8797, 2008, A2. Location in patent: Page/Page column 58 [4] Patent: WO2007/121453, 2007, A2. Location in patent: Page/Page column 108 [5] Patent: WO2017/105565, 2017, A2. Location in patent: Paragraph 0109 |
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