ChemicalBook CAS DataBase List 5-(2-PYRIDYL)-1,2-DIHYDROPYRIDIN-2-ONE

5-(2-PYRIDYL)-1,2-DIHYDROPYRIDIN-2-ONE synthesis

13synthesis methods

Product Name:5-(2-PYRIDYL)-1,2-DIHYDROPYRIDIN-2-ONE
CAS Number:381233-78-9
Molecular formula:C10H8N2O
Molecular Weight:172.18

5-(2-Pyridinyl)-1,2-dihydropyridin-2-one can be used as a pharmaceutical intermediate and biological small molecule additive, mainly in laboratory research. It can synthezied by Suzuki reaction of 2-Bromopyridine and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-ol catalyzed by tetrakis(triphenylphosphine) palladium(0) .

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71-36-3 Synthesis

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Yield:381233-78-9 188g (66%)

Reaction Conditions:

with hydrogenchloride;sodium hydroxide

Steps:

5-Pyridin-2-yl-2(1H)-pyridone
5-Pyridin-2-yl-2(1H)-pyridone A mixture of 2-methoxy-5-pyridin-2-yl-pyridine (550g) and a 4mol/L aquesous solution of hydrochloric acid (2.4L) was heated under reflux for 3 hours. After cooling the reaction solution, and washed with tert-butylmethyl ether (2.2L). To the aqueous layer was added 8mol/L aqueous solution of sodium hydroxide (1.1L) under cooling with ice-water, and then the mixture was washed twice with tert-butylmethyl ether (2.2L). Then, it was adjusted to pH 8 with concentrated hydrochloric acid (310ml) and 8mol/L aqueous solution of sodium hydroxide (100ml), followed by partitioning between 1-butanol (4.5L) and brine (1.8L). The aqueous layer was extracted again with 1-butanol (4.5L), and the combined organic layer was evaporated at 45-50°C. To the resulting residue was added tert-butylmethyl ether (2.2L), to give crystals. The resulting crystals were collected by filtration under reduced pressure and air-dried at 60°C. Then, water (1.6L) was added thereto to dissolve under heating. Then the mixture was water-cooled, and recrystallized. The resulting crystals were collected by filtration under reduced pressure and air-dried at 60°C, to give 188g (66%) of the title compound as grayish white crystals. ¹H-NMR (DMSO-d₆,400MHz): 6.42 (1H, d), 7.19-7.26 (1H, m), 7.74-7.81 (2H,m), 8.11 (1H,d), 8.17 (1H,dd), 8.52-8.55 (1H,m). MS: MH⁺173

References:

Eisai Co., Ltd. EP1300396, 2003, A1

109-04-6 Synthesis