Acetic Acid → HCID 21265856, compound

Temperature

100 °C

2-(Imidazo[1,5-a]pyridin-3-yl)acetonitrile (4.65 g) was dissolved in acetic acid (26 ml). To the solution was added 50%(v/v) sulfuric acid (52 ml), and the mixture was stirred for 3 hours at 100° C., followed by distilling off acetic acid under reduced pressure. To the residue was added, in limited amounts, sodium hydrogencarbonate, and the mixture was concentrated to dryness. To the residue was added methanol (200 ml), then insolubles were filtered off. To the filtrate was added a 4N HCl ethyl acetate solution (40 ml). The mixture was stirred for 15 hours at 25° C., followed by concentration under reduced pressure. To the concentrate were added a 5% aqueous solution of sodium hydrogencarbonate (100 ml) and ethyl acetate (200 ml). The mixture was shaken and left standing to form two layers. The organic layer was dried over anhydrous magnesium sulfate and, then, concentrated to afford the title compound (1.85 g).

1. distillationby distilling off acetic acid under reduced pressure
2. additionTo the residue was added, in limited amounts, sodium hydrogencarbonate
3. concentrationthe mixture was concentrated to dryness
4. additionTo the residue was added methanol (200 ml)
5. filtrationinsolubles were filtered off
6. additionTo the filtrate was added a 4N HCl ethyl acetate solution (40 ml)
7. stirringThe mixture was stirred for 15 hours at 25° C.
8. concentrationfollowed by concentration under reduced pressure
9. additionTo the concentrate were added a 5% aqueous solution of sodium hydrogencarbonate (100 ml) and ethyl acetate (200 ml)
10. stirringThe mixture was shaken
11. waitleft
12. customto form two layers
13. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
14. concentrationconcentrated

ORD record

ord-c6254060cd574ef2a0d44395273e2dad

Source dataset

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06174877B1