Triethylamine → HCID 69002824, compound

Under a nitrogen atmosphere, triethylamine (14.19 mL, 101.8 mmol, 1.5 eq) was added in a single portion to a mixture of 2,4-dichloro-5,6-dimethyl-3-nitropyridine (15.0 g, 67.86 mmol, 1.0 eq) and N,N-dimethylformamide (DMF) (200 mL). The reaction mixture was stirred for 10 minutes, 4-amino-1-butanol (8.76 mL, 95 mmol, 1.4 eq) in DMF (20 mL) was added, and the reaction mixture was stirred overnight. The reaction mixture was concentrated under reduced pressure to provide crude product as an oil. The oil was partitioned between ethyl acetate (300 mL) and water (50 mL). The aqueous layer was back-extracted with ethyl acetate (2×50 mL). The combined organic phases were separated, washed with water (3×30 mL) and brine (30 mL), dried over magnesium sulfate, filtered, and then concentrated under reduced pressure to provide an orange solid. This material was recrystallized from ethyl acetate/hexanes to provide 12.2 g of 4-(2-chloro-5,6-dimethyl-3-nitropyridin-1-yl)butan-1-ol.

1. stirringthe reaction mixture was stirred overnight
2. concentrationThe reaction mixture was concentrated under reduced pressure
3. customto provide crude product as an oil
4. customThe oil was partitioned between ethyl acetate (300 mL) and water (50 mL)
5. extractionThe aqueous layer was back-extracted with ethyl acetate (2×50 mL)
6. customThe combined organic phases were separated
7. washwashed with water (3×30 mL) and brine (30 mL)
8. dry with materialdried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customto provide an orange solid
12. customThis material was recrystallized from ethyl acetate/hexanes

ORD record

ord-8d6763dcbe2d4763b8f3a0c8ecec8840

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08778963B2