Pyridine → HCID 22933738, compound

Temperature

100 °C

A 20%-aqueous sulfuric acid solution (4 ml) was added dropwise to a solution of 4-[(2,2-dimethylpropanoyl)amino]-2-methoxy-3-methylphenyl methanesulfonate (223 mg, 0.707 mmol) in n-butanol (2 ml) at room temperature, and the resulting mixture was heated to 100° C. After 14 hours, the reaction solution was poured onto ice (50 ml) and adjusted to pH 11 with an aqueous sodium hydroxide solution. The resulting mixture was extracted with ethyl acetate (50 ml×3) and the organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure, and to a solution of the resulting residue in ethyl acetate (5 ml) were added pyridine (0.069 ml, 0.848 mmol) and acetic anhydride (0.073 ml, 0.778 mmol) at room temperature. The resulting mixture was heated to 60° C. After 2 hours, the reaction solution was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate→chloroform/ethyl acetate) to obtain 4-(acetylamino)-2-methoxy-3-methylphenyl methanesulfonate (154 mg, 79%).

1. additionthe reaction solution was poured onto ice (50 ml)
2. extractionThe resulting mixture was extracted with ethyl acetate (50 ml×3)
3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
4. customThe organic layer dried
5. concentrationwas concentrated under reduced pressure
6. temperatureThe resulting mixture was heated to 60° C
7. waitAfter 2 hours
8. concentrationthe reaction solution was concentrated under reduced pressure
9. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate→chloroform/ethyl acetate)

ORD record

ord-9856a782ac684cf1908b304225ec16ba

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07199147B2