Sodium Bicarbonate → 3-Hydroxy-6-n-propylpyridine

Participants

Reaction Conditions

Reaction Steps

5-Amino-2-n-propylpyridine (70.3 g, 516 mmol) was dissolved in 1300 ml of 1M hydrochloric acid and sodium nitrite (35.6 g, 516 mmol) dissolved in 300 ml of water was added dropwise at 0° C. The reaction mixture was stirred at 0° C. for 1/2 hour, heated to 70° C. for 2 hours, and then stirred at room temperature the overnight. The reaction mixture was neutralised to pH=8 by adding solid sodium hydrogen carbonate, and the product was extracted into ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, and the solvent was evaporated. The crude product was purified by column chromatography over silica gel 60, using ethyl acetate:petroleum ether (1:1) as the eluent. This gave 65.7 g (92%) of 5-hydroxy-2-n-propylpyridine as an orange wax. 1H-NMR (CDCl3, 200 MHz) δ: 0.91 (t, 3H); 1.68 (sext, 2H); 2.71 (t, 2H); 7.09 (d, 1H); 7.25 (dd, 1H); 8.13 (d, 1H); 11.79 (s, 1H).

Provenance & Evidence