Hydrochloric Acid → HCID 67072510, compound

Temperature

80 °C

To a stirring solution of 5-methoxy-2-(4-methoxybenzyl)pyridazin-3(2H)-one (117 mg, 0.47 mmol) in THF (3 mL) at room temperature under argon was added 1M NaOH (2.0 mL, 2.0 mmol). The resulting reaction mixture was heated at 80° C. under argon for a day and monitored by LCMS until the reaction was completed. EtOAc (20 mL), 1 M HCl (2 mL), and water (10 mL) were added to the reaction mixture. Layers were separated. Organic layer were washed with water (15 mL), and brine (15 mL). Organic phase was dried (MgSO4), filtered and concentrated. The crude product was dissolved in a small amount of DCM (˜2 ml) and loaded onto a 40 g ISCO silica gel column which was eluted with a 20 min gradient from 20% to 100% EtOAc/Hexanes. 95 mg (77%) of 5-hydroxy-2-(4-methoxybenzyl)pyridazin-3(2H)-one was obtained as a gum. MS (ESI) 233 (M+H).

1. customThe resulting reaction mixture
2. customLayers were separated
3. washOrganic layer were washed with water (15 mL), and brine (15 mL)
4. dry with materialOrganic phase was dried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated
7. dissolutionThe crude product was dissolved in a small amount of DCM (˜2 ml)
8. washwas eluted with a 20 min gradient from 20% to 100% EtOAc/Hexanes

ORD record

ord-951e83104c2c4339a79fa539cca1ee95

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08372837B2