Acetic Acid → N-(2-(6-chloropyridin-3-yl)propan-2-yl)acetamide

2-(6-chloropyridin-3-yl)propan-2-ol (637 mg, 3.71 mmol, Eq: 1.00) was dissolved in acetonitrile (5 ml). Acetic acid (2.9 g, 2.76 ml, 48.3 mmol, Eq: 13) was added at room temperature and cooled after the addition to 0° C. Sulfuric acid, concentrated (5.1 g, 2.77 ml, 52.0 mmol, Eq: 14) was added dropwise to the solution, then allowed to warm up to room temperature and stirred over night. The reaction mixture was poured into ice, concentrated NaOH solution was added until pH was basic; extracted with ethyl acetate; org. phase was washed with brine; dried with sodium sulfate; filtered to give a yellow solid. This residue was triturated with ethyl acetate and a little bit hexane. Resulting precipitate was filtered off to give a white solid (338 mg, 1.59 mmol).

1. temperaturecooled
2. additionafter the addition to 0° C
3. concentrationSulfuric acid, concentrated (5.1 g, 2.77 ml, 52.0 mmol, Eq: 14)
4. additionwas added dropwise to the solution
5. additionThe reaction mixture was poured into ice, concentrated NaOH solution
6. additionwas added until pH
7. extractionextracted with ethyl acetate
8. washphase was washed with brine
9. dry with materialdried with sodium sulfate
10. filtrationfiltered
11. customto give a yellow solid
12. customThis residue was triturated with ethyl acetate
13. customResulting precipitate
14. filtrationwas filtered off

ORD record

ord-d7d080f74fd141f6b36046583aa75204

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08481540B2