Acetic Anhydride → HCID 59131061, compound

Temperature

50 °C

Acetic anhydride (21 mL, 223 mmol) was added to a solution of 2-amino-3-bromo-6-picoline (10 g, 53.46 mmol) in dioxan (50 mL) and the mixture was stirred at 50° C. for 18 hours. The solvent was then evaporated under reduced pressure and the residue was diluted with saturated sodium hydrogen carbonate solution (150 mL). The precipitate was filtered off, washed with water and re-dissolved in dichloromethane, and the filtrate was neutralised to pH7 with saturated sodium hydrogen carbonate solution and extracted with dichloromethane (3×100 mL). The organic solutions were combined, washed with water, dried over magnesium sulfate and concentrated in vacuo to give a white solid. Purification of the solid by column chromatography on silica gel, eluting with ethyl acetate:heptane, 75:25, afforded the title compound as a white solid in 75% yield, 9.2 g.

1. customThe solvent was then evaporated under reduced pressure
2. additionthe residue was diluted with saturated sodium hydrogen carbonate solution (150 mL)
3. filtrationThe precipitate was filtered off
4. washwashed with water
5. dissolutionre-dissolved in dichloromethane
6. extractionextracted with dichloromethane (3×100 mL)
7. washwashed with water
8. dry with materialdried over magnesium sulfate
9. concentrationconcentrated in vacuo
10. customto give a white solid
11. customPurification of the solid by column chromatography on silica gel
12. washeluting with ethyl acetate

ORD record

ord-d2a2373512684bb88a59bc8e1f04c59c

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07649004B2