Ethyl Acetate → 6-Chloropyridine-2,3-diamine

Temperature

60 °C

A flask was charged with 6-chloro-3-nitropyridin-2-amine (500 mg, 2.88 mmol) and tin(II) chloride dihydrate (3.25 g, 14.40 mmol) under argon. A 9:1 mixture of ethyl acetate:2-methyl-2-propanol was then added, and the reaction was allowed to stir at 60° C. for one hour. Sodium borohydride (55 mg, 1.44 mmol) was then added, and the reaction was allowed to stir for 3 hours at 60° C. The reaction mixture was then cooled and the solvent evaporated under reduced pressure. The solid was taken up in water and saturated aqueous sodium carbonate was added until pH˜7 was attained. The mixture was extracted with ethyl acetate (2×). The combined organics were washed with brine, and dried over magnesium sulfate. This mixture was filtered and the filtrate concentrated under reduced pressure. Recrystallization from ethyl acetate/hexanes afforded the title compound.

1. stirringto stir for 3 hours at 60° C
2. temperatureThe reaction mixture was then cooled
3. customthe solvent evaporated under reduced pressure
4. additionsaturated aqueous sodium carbonate was added until pH˜7
5. extractionThe mixture was extracted with ethyl acetate (2×)
6. washThe combined organics were washed with brine
7. dry with materialdried over magnesium sulfate
8. filtrationThis mixture was filtered
9. concentrationthe filtrate concentrated under reduced pressure
10. customRecrystallization from ethyl acetate/hexanes

ORD record

ord-0de45460001f47119016d5b16584a08e

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08344144B2