Methyl iodide → 5-Methoxy-2-nitrobenzaldehyde

To a solution of 5-hydroxy-2-nitrobenzaldehyde (300 mg, 1.80 mmol) in 3.6 mL of dry N,N-dimethylformamide was added sodium hydride (94 mg, 55%, 2.1 mmol) under nitrogen at 0° C. After the reaction mixture was stirred at room temperature for 30 min, methyl iodide (0.17 mL, 2.7 mmol) was added with additional stirring for 30 min. After the reaction mixture was quenched with saturated NH4Cl aqueous solution at 0° C., the solution was extracted with ether. The extract was washed with saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20 to 70/30) to obtain the title compound as a slightly yellow powder (298 mg, 91%).

1. stirringwith additional stirring for 30 min
2. customAfter the reaction mixture was quenched with saturated NH4Cl aqueous solution at 0° C.
3. extractionthe solution was extracted with ether
4. washThe extract was washed with saturated NaHCO3 aqueous solution, brine
5. dry with materialdried over MgSO4
6. filtrationAfter filtration
7. concentrationthe filtrate was concentrated in vacuo
8. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20 to 70/30)

ORD record

ord-e0bace273b4b4436b16ded95ad323a5e

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08552220B2