反应详情

Potassium carbonate (36.3 g, 263 mmol) was added to 3-chloroisonicotinic acid (10.35 g, 65.7 mmol) in DMSO (50 mL). After 30 min, MeI (8.22 mL, 131 mmol) was added. The mixture was stirred at room temperature for 2 h, quenched with saturated NH4Cl (300 mL) and water (200 mL), and extracted with EtOAc (3×200 mL). The combined extracts were washed with brine (2×50 mL), dried (MgSO4) and concentrated. Silica gel chromatography, eluting with 10-30% ethyl acetate in hexanes, gave methyl 3-chloroisonicotinate as a colorless liquid (6.275 g, 56% yield). MS (ES+) m/z: 172 (M+H); LC retention time: 2.45 min (analytical HPLC Method A).

1. customquenched with saturated NH4Cl (300 mL) and water (200 mL)
2. extractionextracted with EtOAc (3×200 mL)
3. washThe combined extracts were washed with brine (2×50 mL)
4. dry with materialdried (MgSO4)
5. concentrationconcentrated
6. washSilica gel chromatography, eluting with 10-30% ethyl acetate in hexanes