1-Methyl-2(1H)-pyridinone → 1-Methyl-6-oxo-1,6-dihydropyridine-3-sulfonic acid, ammonium salt

Temperature

50 °C

Chlorosulphonic acid (2 ml, 30.1 mmol) was added cautiously dropwise by pipette over 5 minutes to stirred neat 1-methylpyridin-2(1H)-one (8.09 ml, 82 mmol) and the resulting viscous solution was stirred at 50° C. for 40 hours. The cooled solidified reaction mixture was then added cautiously to water (100 ml), giving a clear brown solution. This solution was concentrated in vacuo to 40 ml, then made basic with concentrated ammonia solution, and washed with dichloromethane (6×100 ml). The aqueous phase was then evaporated to give a brown slurry which was triturated in methanol and filtered. The filtrate was evaporated to give 1-methyl-6-oxo-1,6-dihydropyridine-3-sulfonic acid, ammonium salt (3 g) as a brown solid. LCMS (Method F, ES-API): RT 0.46 min, m−H=188.0.

1. customgiving a clear brown solution
2. concentrationThis solution was concentrated in vacuo to 40 ml
3. washwashed with dichloromethane (6×100 ml)
4. customThe aqueous phase was then evaporated
5. customto give a brown slurry which
6. customwas triturated in methanol
7. filtrationfiltered
8. customThe filtrate was evaporated

ORD record

ord-ef170e70f33c4e3fa83ab664e4c0dc3a

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08859774B2