Acetic Acid → 5-Bromo-6-chloropyridin-3-amine

To a stirred mixture of 3-bromo-2-chloro-5-nitropyridine (10.00 g, 42.1 mmol) and acetic acid (12.16 mL, 211 mmol) in water (100 mL) at 0° C. was added iron (11.76 g, 211 mmol, powder −325 mesh). The mixture was warmed to room temperature and stirred for 4 h. The reaction mixture was filtered and washed with water. The filtrate was then extracted with EtOAc. The filter cake was then washed with EtOAc, and the resulting filtrate was combined with the previous organic layer from the aqueous extraction. The two organic mixtures were then washed with water (2×), washed with sat. sodium chloride, dried over magnesium sulfate, filtered, and concentrated to give 5-bromo-6-chloropyridin-3-amine. MS (ESI, pos. ion) m/z: 207.9 and 209.9 (M+1).

1. filtrationThe reaction mixture was filtered
2. washwashed with water
3. extractionThe filtrate was then extracted with EtOAc
4. washThe filter cake was then washed with EtOAc
5. extractionthe resulting filtrate was combined with the previous organic layer from the aqueous extraction
6. washThe two organic mixtures were then washed with water (2×)
7. washwashed with sat. sodium chloride
8. dry with materialdried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-0f044e3b34fd4be0affdabf0c8225407

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08637500B2