Water → 4-(4-Fluorobenzyloxy)-1h-pyridin-2-one

HRID 1044421Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:13]=[CH:12][NH:11][C:10](=[O:14])[CH:9]=1.Cl[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1.O>CN(C=O)C>[F:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][O:7][C:8]2[CH:13]=[CH:12][NH:11][C:10](=[O:14])[CH:9]=2)=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of potassium carbonate (12.44 g, 90 mmol), 4-hydroxypyridin-2(1H)-one (10 g, 90 mmol) in DMF (500 mL) was stirred at 140° C. for 60 min prior to addition of a solution of 1-(chloromethyl)-4-fluorobenzene (13.01 g, 90 mmol) in DMF (5.0 mL). After stirring at 140° C. for 60 min, the reaction was cooled to RT prior to dilution with water (1.0 L). The resulting suspension was stirred at RT for 60 min prior to collection of precipitate by filtration. The filter cake was washed with water (250 mL), suspended with stirring in ethyl ether (500 mL) for 15 min and collected by filtration. After air-drying, 4-(4-fluorobenzyloxy)pyridin-2(1H)-one 17A was obtained as a white solid (6.67 g, 28.9 mmol, 32.1% yield). 1H NMR (400 MHz, MeOD) δ ppm 7.42-7.56 (2H, m), 7.34 (1H, d, J=7.26 Hz), 7.03-7.25 (2H, m), 6.12-6.24 (1H, m), 6.01 (1H, br. s.), 5.10 (2H, s).

Workup

stirringAfter stirring at 140° C. for 60 min
temperaturethe reaction was cooled to RT
stirringThe resulting suspension was stirred at RT for 60 min
customto collection of precipitate
filtrationby filtration
washThe filter cake was washed with water (250 mL)
stirringwith stirring in ethyl ether (500 mL) for 15 min
filtrationcollected by filtration
customAfter air-drying

Sources & evidence

ORD record: ord-fa7ea452dda545198252696a3c14e553
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563583B2

Reaction notes

Loading…