Pyridine → HCID 18447399, compound

To a solution of 2-methoxy-1-(methoxymethoxy)-4-nitrobenzene (1.2 g, 5.63 mmol) in ethyl acetate (30 ml) was added 10%-Pd/C (120 mg) at room temperature, and reaction was carried out under a hydrogen atmosphere. After 30 minutes, the mixture thus obtained was filtered by the use of Celite and the filtrate was concentrated under reduced pressure. To a solution of the resulting residue in ethyl acetate (30 ml) were added pyridine (0.546 ml, 6.75 mmol) and pivaloyl chloride (0.763 ml, 6.19 mmol) at 0° C., and the resulting mixture was warmed up to room temperature. After 15 hours, a saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution and the resulting mixture was poured into water (100 ml) and extracted with ethyl acetate (50 ml×2), and the organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain N-[3-methoxy-4-(methoxymethoxy)phenyl]-2,2-dimethylpropanamide (1.48 g, 98%).

1. customreaction
2. customthe mixture thus obtained
3. filtrationwas filtered by the use of Celite
4. concentrationthe filtrate was concentrated under reduced pressure
5. waitAfter 15 hours
6. extractionextracted with ethyl acetate (50 ml×2)
7. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
8. customThe organic layer dried
9. concentrationwas concentrated under reduced pressure
10. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)

ORD record

ord-0cc0fa7d068449cf880c5d3571a448aa

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07199147B2