Dimethylformamide → HCID 93083642, compound

A 100-mL round bottomed flask equipped with a magnetic stir bar was charged with 2-chloro-3-nitropyridine (4.0 g, 25.2 mmol), potassium carbonate (4.18 g, 30.3 mmol), and DMF (25 mL). Next, (S)-2-aminopropane-1-ol (1.990 g, 26.5 mmol) was added at rt. The yellow mixture was stirred at rt for 45 min, then was heated to 50° C. for 22 h. Heating was discontinued, and after the mixture had cooled, it was diluted with water (50 mL) and extracted with ethyl acetate. The organic phase was separated and washed with 5% aqueous sodium chloride solution (3×25 mL). The combined aqueous layers were extracted with ethyl acetate. The combined organic phases were concentrated to yield (S)-2-(3-nitropyridin-2-ylamino)propane-1-ol (5.68 g, 28.8 mmol, 114%) as a dark yellow syrup. MS (ESI, pos. ion) m/z 198 [M+1]+.

1. customA 100-mL round bottomed flask equipped with a magnetic stir bar
2. temperaturewas heated to 50° C. for 22 h
3. temperatureHeating
4. temperatureafter the mixture had cooled
5. extractionextracted with ethyl acetate
6. customThe organic phase was separated
7. washwashed with 5% aqueous sodium chloride solution (3×25 mL)
8. extractionThe combined aqueous layers were extracted with ethyl acetate
9. concentrationThe combined organic phases were concentrated

ORD record

ord-63a164373ba740d8816d6a102a4bbd29

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09422281B2