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147269-67-8

147269-67-8 Structure

147269-67-8 Structure
IdentificationBack Directory
[Name]

BENZYL 2-OXO-1,2-DIHYDROPYRIDIN-3-YLCARBAMATE
[CAS]

147269-67-8
[Synonyms]

benzyl 2-hydroxypyridin-3-ylcarbaMate
BENZYL 2-OXO-1,2-DIHYDROPYRIDIN-3-YLCARBAMATE
benzyl N-(2-oxo-1,2-dihydropyridin-3-yl)carbaMate
(2-Oxo-1,2-dihydropyridin-3-yl)carbamic acid benzyl ester
BENZYL 2-OXO-1,2-DIHYDROPYRIDIN-3-YLCARBAMATE ISO 9001:2015 REACH
Carbamic acid, N-(1,2-dihydro-2-oxo-3-pyridinyl)-, phenylmethyl ester
[Molecular Formula]

C13H12N2O3
[MDL Number]

MFCD07772020
[MOL File]

147269-67-8.mol
[Molecular Weight]

244.25
Chemical PropertiesBack Directory
[Melting point ]

175-178 °C
[Boiling point ]

474.3±45.0 °C(Predicted)
[density ]

1.29±0.1 g/cm3(Predicted)
[storage temp. ]

Sealed in dry,2-8°C
[pka]

8.52±0.20(Predicted)
[Appearance]

Off-white to pink Solid
Spectrum DetailBack Directory
[Spectrum Detail]

BENZYL 2-OXO-1,2-DIHYDROPYRIDIN-3-YLCARBAMATE(147269-67-8)1HNMR
Hazard InformationBack Directory
[Synthesis]

3-Amino-2(1H)-pyridinone

33630-99-8

Benzyl chloroformate

501-53-1

BENZYL 2-OXO-1,2-DIHYDROPYRIDIN-3-YLCARBAMATE

147269-67-8

At room temperature, 3-aminopyridin-2(1H)-one (3.25 g, 29.5 mmol) and sodium carbonate (6.26 g, 59.0 mmol) were dissolved in tetrahydrofuran (100 mL), and benzyl chloroformate (5.27 mL, 36.9 mmol) was added slowly and dropwise. The reaction mixture was stirred at room temperature for 24 hours. Upon completion of the reaction, the reaction mixture was diluted with ethyl acetate (150 mL) and filtered through Celite. The filtrate was concentrated under reduced pressure to about 200 mL and subsequently washed with water (40 mL) and dried with anhydrous magnesium sulfate. It was again concentrated under reduced pressure to about 50 mL and the precipitated white solid (first product) was collected by filtration. The remaining filtrate was concentrated to near dryness under reduced pressure and the residue was stirred with ether (50 mL) and the insoluble white solid (second batch of product) was collected by diafiltration. The two batches of products were combined and dried under vacuum at 50 °C to afford the target compound (2-oxo-1,2-dihydropyridin-3-yl)carbamic acid benzyl ester (5.77 g, 23.62 mmol, 80% yield) as a white solid.

[References]

[1] ChemMedChem, 2011, vol. 6, # 7, p. 1228 - 1237
[2] Patent: WO2007/27729, 2007, A1. Location in patent: Page/Page column 39-40
[3] Patent: WO2015/89143, 2015, A1. Location in patent: Page/Page column 83; 84
[4] Journal of Medicinal Chemistry, 1994, vol. 37, # 19, p. 3090 - 3099
[5] Patent: US2007/287696, 2007, A1. Location in patent: Page/Page column 33
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