Phosphorus oxychloride → 2-Chloro-6-isopropyl-pyridin-4-ylamine

A mixture of 4-amino-6-isopropyl-3-nitro-1H-pyridin-2-one (555 mg, 2.81 mmol) in POCl3 (10 mL) is stirred at reflux under N2 for 1.5 h. After cooling, the solution is concentrated in vacuo. The reaction flask is then placed in an ice bath, and crushed ice (˜20 g) is added to the residue. The mixture is swirled vigorously for several minutes and then stirred at room temperature for 30 min. The mixture is then extracted with EtOAc. The extract is washed with an additional 20 mL of H2O. The aqueous washes are reextracted once with EtOAc, and the combined extracts are dried over Na2SO4 and concentrated, yielding 2-chloro-6-isopropyl-pyridin-4-ylamine as an orange oil. This material is used without further purification, 1H NMR (DMSO-d6, 300 MHz) δ 7.27 (br s, 2H), 6.65 (s, 1H), 2.77 (sept, J=6.9 Hz, 1H), 1.13 (d, J=6.9 Hz, 6H) ppm.

1. temperatureat reflux under N2 for 1.5 h
2. temperatureAfter cooling
3. concentrationthe solution is concentrated in vacuo
4. customThe reaction flask is then placed in an ice bath
5. customcrushed ice (˜20 g)
6. additionis added to the residue
7. waitThe mixture is swirled vigorously for several minutes
8. stirringstirred at room temperature for 30 min
9. extractionThe mixture is then extracted with EtOAc
10. washThe extract is washed with an additional 20 mL of H2O
11. dry with materialthe combined extracts are dried over Na2SO4
12. concentrationconcentrated

ORDレコード

ord-16f3acf1c4dc4e739f6a585a33db3a24

出典データセット

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07642267B2