反应详情

温度

100 °C

To a solution of 4-aminophenol (3.6 g, 32.8 mmol) and 4-chloropicoline (5.0 g, 39.3 mmol) in anh DMPU (50 mL) was added potassium tert-butoxide (7.4 g, 65.6 mmol) in one portion. The reaction mixture was heated at 100° C. with stirring for 18 h, then was allowed to cool to room temp. The resulting mixture was poured into water (200 mL) and extracted with EtOAc (3×150 mL). The combined extracts were sequentially washed with water (3×100 mL) and a saturated NaCl solution (2×100 mL), dried (Na2SO4), and concentrated in vacuo. The resulting oil was purified by flash chromatography (50% EtOAc/50% hexane) to afford the desired product as a yellow oil (0.7 g, 9%): CI-MS m/z 201 ((M+H)+). A14c. General Method for Substituted Aniline Synthesis via Nucleophilic Aromatic Substitution using a Halopyridine

1. temperatureto cool to room temp
2. extractionextracted with EtOAc (3×150 mL)
3. washThe combined extracts were sequentially washed with water (3×100 mL)
4. dry with materiala saturated NaCl solution (2×100 mL), dried (Na2SO4)
5. concentrationconcentrated in vacuo
6. customThe resulting oil was purified by flash chromatography (50% EtOAc/50% hexane)