Ammonium formate → 6-Isopropoxypyridin-3-OL

5-Chloro-6-isopropoxypyridin-3-ol (0.288 g, 1.54 mmol) was dissolved in absolute ethanol (5 mL) and heated to reflux. Then 10% palladium on Carbon (0.085 g, 0.799 mmol) and ammonium formate (1.35 g, 0.0214 mol) were added and the mixture was stirred at reflux under nitrogen for one hour. The reaction mixture was filtered on a pad of Arbocel® under a nitrogen stream and washed with MeOH (15 mL). The filtrate was concentrated in vacuo. The resulting crude was then diluted in EtOAc (20 mL) and washed with water (30 mL). The organic layer was then dried over sodium sulfate, filtered, and concentrated in vacuo to give title compound as a white solid (0.23 g, 97%):

1. temperatureheated to reflux
2. temperatureat reflux under nitrogen for one hour
3. filtrationThe reaction mixture was filtered on a pad of Arbocel® under a nitrogen stream
4. washwashed with MeOH (15 mL)
5. concentrationThe filtrate was concentrated in vacuo
6. additionThe resulting crude was then diluted in EtOAc (20 mL)
7. washwashed with water (30 mL)
8. dry with materialThe organic layer was then dried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD record

ord-dc36f9938a20402aa70ad8957a6b620f

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08592629B2