Acetic Acid → 5-Fluoro-2,3-pyridinediamine

To a stirred mixture of 2-amino-5-fluoro-3-nitropyridine (2.46 g, 15.66 mmol) in a mixture of glacial HOAc (10 mL) and MeOH (20 mL) at 0° C. was added zinc dust (5.09 g, 78.3 mmol) portion-wise, and the mixture was allowed to warm slowly to rt. After stirring at rt for 15 h, the mixture was filtered through Celite and the filtrate was concentrated under reduced pressure. The residue was partitioned between EtOAc and saturated aq NaHCO3. The organic layer was separated and the aqueous layer was extracted with additional EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure to afford 5-fluoropyridine-2,3-diamine (1.13 g) as a solid which was not purified further. LCMS (ESI) m/z 128 (M+H)+.

1. filtrationthe mixture was filtered through Celite
2. concentrationthe filtrate was concentrated under reduced pressure
3. customThe residue was partitioned between EtOAc and saturated aq NaHCO3
4. customThe organic layer was separated
5. extractionthe aqueous layer was extracted with additional EtOAc
6. dry with materialThe combined organic layers were dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure

ORD record

ord-b02ea065594c4886a66085722ef07bf8

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952058B2