Potassium Carbonate → 1-(4-Chlorobutyl)-3-methoxy-1H-pyridin-2-one

A mixture of 3-methoxy-2(1H)-pyridone (0.54 g, 4.31 mmol) and potassium carbonate (0.71 g, 5.14 mmol) in anhydrous N,N-dimethylformamide (20 mL) was stirred at room temperature for 1 h. 1-Bromo-4-chlorobutane (0.50 mL, 4.33 mmol) was then added and the resulting reaction mixture was stirred at room temperature overnight. The reaction mixture was quenched with water (20 mL) and extracted with dichloromethane (3×30 mL). The organic layers were collected, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel, eluting with 100% dichloromethane and 5% methanol in dichloromethane to afford the title compound as a pale yellow oil (0.39 g, 42%). 1H NMR (400 MHz, CDCl3) δ ppm 6.87 (dd, 1H) 6.59 (dd, 1H) 6.10 (t, 1H) 4.02 (t, 2H) 3.81 (s, 3H) 3.57 (t, 2H) 2.01-1.87 (m, 2H) 1.87-1.73 (m, 2H).

1. customthe resulting reaction mixture
2. stirringwas stirred at room temperature overnight
3. customThe reaction mixture was quenched with water (20 mL)
4. extractionextracted with dichloromethane (3×30 mL)
5. customThe organic layers were collected
6. dry with materialdried over Na2SO4
7. concentrationconcentrated in vacuo
8. customThe crude product was purified by flash chromatography on silica gel
9. washeluting with 100% dichloromethane and 5% methanol in dichloromethane

ORD record

ord-bbf6d438eb6642eb867355a05f1b7b6a

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07928108B2