Methanol → HCID 23093513, compound

To a solution of 2-(methylamino)phenyl]methanol (1.37 g: synthesized by a method described in WO 01/32652) in tetrahydrofuran (50 mL) were added pyridine (1.05 mL), acetic anhydride (1.23 mL) and 4-dimethylaminopyridine (0.18 g), and stirred at room temperature for 8 hrs. To the reaction solution was added water (100 mL), and extracted with ethyl acetate (50 mL). The organic layer was washed sequentially with 5% aqueous solution of copper (II) sulfate (50 mL), saturated aqueous solution of sodium bicarbonate (50 mL), and saturated brine (50 mL), and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified with flash silica gel column chromatography (elute with ethyl acetate:hexane=1:5, then 1:3) to give title compound as white solid (0.38 g).

1. extractionextracted with ethyl acetate (50 mL)
2. washThe organic layer was washed sequentially with 5% aqueous solution of copper (II) sulfate (50 mL), saturated aqueous solution of sodium bicarbonate (50 mL), and saturated brine (50 mL)
3. dry with materialdried over anhydrous magnesium sulfate
4. distillationthe solvent was distilled away under reduced pressure
5. customThe resulting residue was purified with flash silica gel column chromatography (
6. washelute with ethyl acetate

ORD record

ord-0938ec3d08424fc3a45c2fb9f371ae39

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08449911B2