Triethylamine → HCID 21913176, compound

3-Amino-1-propanol (6.92 mL, 90.5 mmol) was added dropwise to a stirred solution of 2,4-dichloro-5,6-dimethyl-3-nitropyridine (20.0 g, 90.5 mmol) and triethylamine (18.9 mL, 136 mmol) in DMF (300 mL) at room temperature. After 16 hours, the solvent was removed under reduced pressure and the resulting oil was partitioned between ethyl acetate (450 mL) and water (50 mL). The layers were separated and the organic layer was washed with water (3×50 mL). The combined aqueous layers were back-extracted with ethyl acetate (2×30 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting orange solid was triturated with hexanes/ethyl acetate (2:1) and was isolated by filtration to yield 12.43 g of 3-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]propan-1-ol as a yellow solid.

1. customthe solvent was removed under reduced pressure
2. customthe resulting oil was partitioned between ethyl acetate (450 mL) and water (50 mL)
3. customThe layers were separated
4. washthe organic layer was washed with water (3×50 mL)
5. extractionThe combined aqueous layers were back-extracted with ethyl acetate (2×30 mL)
6. dry with materialThe combined organic layers were dried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe resulting orange solid was triturated with hexanes/ethyl acetate (2:1)
10. customwas isolated by filtration

ORD record

ord-8eb281fe67004416be90bbac1e84288d

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07648997B2