O-Methylhydroxylamine → 2-Amino-6-methoxy-3-nitropyridine

Temperature

25 °C

6-Methoxy-3-nitropyridine (154 mg, 1 mmol) and O-methylhydroxylamine (71 mg, 1.5 mmol) were dissolved in DMSO (2 ml), and a resulting solution was added dropwise to a DMSO solution (3 ml) containing potassium tert-butoxide (336 mg, 3 mmol) and zinc (II) chloride (136 mg, 1 mmol) at 25° C. After completion of the addition, the resulting mixture was stirred at 25 ° C. for 9 hours and an aqueous saturated ammonium chloride solution (50 ml) was added, followed by extraction with ethyl acetate (80 ml). A resulting organic layer was dried over anhydrous magnesium sulfate, and then isolated and purified by subjection to silica gel thin layer chromatography [eluent: ethyl acetate/hexane=1/1] to obtain 147 mg of 2-amino-6-methoxy-3-nitropyridine (yield: 87%).

1. additionAfter completion of the addition
2. extractionfollowed by extraction with ethyl acetate (80 ml)
3. dry with materialA resulting organic layer was dried over anhydrous magnesium sulfate
4. customisolated
5. custompurified by subjection to silica gel thin layer chromatography [eluent: ethyl acetate/hexane=1/1]

ORD record

ord-e2e437f90535462b87ba39f110724f13

Source dataset

uspto-grants-1997_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05648496