Sodium Hydroxide → HCID 55253214, compound

Temperature

0 °C

To a solution of 6-methoxy-3-nitropicolinonitrile (Piersanti, G. et al. Org. Biommolecular Chem. 2007, 5, 2567-2571.) (2.0 g, 11.1 mmol) in diglyme (52 mL) was added dropwise a solution of SnCl2 (6.35 g, 33.5 mmol) in concentrated HCl solution (26 mL) at 0° C. The solution was stirred at 0° C. for 1 hr, then the reaction mixture was neutralized with concentrated NaOH solution, and extracted with EtOAc (2×). The combined organic layers were washed with brine, and dried over Na2SO4. After evaporation of the solvent, the residue was purified by chromatography on silica gel (50% EtOAc in hexanes) to give 3-amino-6-methoxypicolinonitrile (966 mg, 58%) as a brown solid. 1H NMR (400 MHz, CDCl3) δ 3.81 (s, 3H), 4.10 (bs, 2H), 6.81 (d, J=8.0 Hz, 1H), 7.08 (d, J=8.0 Hz, 1H). MS 150 (MH+).

1. extractionextracted with EtOAc (2×)
2. washThe combined organic layers were washed with brine
3. dry with materialdried over Na2SO4
4. customAfter evaporation of the solvent
5. customthe residue was purified by chromatography on silica gel (50% EtOAc in hexanes)

ORD record

ord-df0d627b4f6641c282bd09ed03c4c510

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09000054B2