152398-05-5

White solid

Step 2: Three aliquots were carefully added to an anhydrous THF (200 mL) slurry of solid compound 3-aminoisonicotinic acid (9.5 g, 69 mmol) to LiAlH4 (9.5 g, 250 mmol). The resulting reaction mixture was stirred at room temperature for 2 days. Upon completion of the reaction, it was cooled in an ice bath and water (10 mL), 15% NaOH aqueous solution (10 mL) and water (30 mL) were added sequentially dropwise to quench the reaction. The reaction mixture was filtered through a diatomaceous earth pad and washed several times with THF. After evaporation of the solvent, the resulting oil solidified on standing. The reaction mixture was purified using silica gel fast chromatography with 5% CH3OH (containing NH3)/EtOAc as eluent to afford the target product 3-amino-4-hydroxymethylpyridine 6.21 g (72% yield).LC-MS: m/z = 125 ([M+H]+).

[1] Patent: WO2004/831, 2003, A1. Location in patent: Page 22
[2] Patent: WO2008/108957, 2008, A2. Location in patent: Page/Page column 95
[3] Australian Journal of Chemistry, 1993, vol. 46, # 7, p. 987 - 993
[4] Patent: WO2011/38572, 2011, A1. Location in patent: Page/Page column 71; 72