Isobutylamine → HCID 86227608, compound

A solution of 2,4-dichloro-5,6-dimethyl-3-nitropyridine (40.0 g, 181 mmol), triethylamine (26.5 mL, 190 mmol), and isobutyl amine (18.9 mL, 190 mmol) in N,N-dimethylformamide (500 mL) was stirred at room temperature over night. The solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (500 mL) and washed with water (3×80 mL) and brine (40 mL). The aqueous was extracted with ethyl acetate (3×50 mL) and the back-extracts washed with water (3×40 mL) and brine (30 mL). The combined organics were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by HPFC eluting with a gradient of 10-30% ethyl acetate in hexanes to give 25.8 g of 2-chloro-N-isobutyl-5,6-dimethyl-3-nitropyridin-4-amine as a yellow oil.

1. customThe solvent was removed under reduced pressure
2. dissolutionThe residue was dissolved in ethyl acetate (500 mL)
3. washwashed with water (3×80 mL) and brine (40 mL)
4. extractionThe aqueous was extracted with ethyl acetate (3×50 mL)
5. washthe back-extracts washed with water (3×40 mL) and brine (30 mL)
6. dry with materialThe combined organics were dried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe crude product was purified by HPFC
10. washeluting with a gradient of 10-30% ethyl acetate in hexanes

ORD record

ord-ecfa86df06de4c2c92a5d5a3303b8142

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07968563B2