Acetic Acid → HCID 58370338, compound

Temperature

80 °C

To a mixture of (4-Methanesulfonyl-2,3-dimethyl-pyridine)-1-oxide (24 g) and acetic acid (50 ml) was added acetic anhydride (28.2 ml), followed by heating to reflux and maintaining the same temperature for about 3 hrs. The reaction mass was cooled to 80° C. and methanol (25 ml) was added followed distilling off the solvent completely under vacuum. THF:methanol (125:25 ml), LiOH (7.5 g) was added to the crude at 25-30° C. followed by adding DCM (100 ml) to the reaction mixture and extraction with (2×150 ml) DCM. All the organic layers were combined and washed with saturated sodium chloride solution (25 ml). The organic layer was dried over sodium sulphate and distilled off completely under vacuum. Subsequently, n-hexane (100 ml) was added to the reaction mass, the compound filtered and washed with n-hexane (10 ml). The wet compound was then dried at 50-55° C. to yield 14 g of the title compound characterized by 1HNMR data (300 MHz): δ 2.58 (s, 3H), 3.13 (s, 3H), 4.62 (s, 1H), 4.80 (s, 2H), 7.86 (d, 1H), 8.68 (d, 1H) and mass [M]+: 202.06.

1. temperatureby heating
2. temperatureto reflux
3. temperaturemaintaining the same temperature for about 3 hrs
4. distillationfollowed distilling off the solvent completely under vacuum
5. additionTHF:methanol (125:25 ml), LiOH (7.5 g) was added to the crude at 25-30° C.
6. additionby adding DCM (100 ml)
7. extractionto the reaction mixture and extraction with (2×150 ml) DCM
8. washwashed with saturated sodium chloride solution (25 ml)
9. dry with materialThe organic layer was dried over sodium sulphate
10. distillationdistilled off completely under vacuum
11. additionSubsequently, n-hexane (100 ml) was added to the reaction mass
12. filtrationthe compound filtered
13. washwashed with n-hexane (10 ml)
14. customThe wet compound was then dried at 50-55° C.

ORD record

ord-4bff9de7dcb84b92b97a6a52e16eac48

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08513427B2