Ammonium Hydroxide → Thieno(2,3-c)pyridine

Participants

Reaction Conditions

Reaction Steps

The material from Step ii (23.5 g, 61.6 mmol), was dissolved in 100 mL CH2Cl2. The three neck flask was fitted with a reflux condenser and internal thermometer under N2 atmosphere. The flask was evacuated and purged with nitrogen. Titanium (IV) chloride (40 mL, 369 mmol) was added to the reaction slowly. The reaction temperature was maintained at around 40° C. After about 15 mL were added, the reaction was placed in an ice bath to control the temperature. The reaction was allowed to gradually warm to room temperature before heating to 40° C. overnight. The reaction was heated to 40° C. for 18 hours, then cooled to room temperature. The reaction contents were poured, in portions, into a large beaker containing 200 g of ice and 200 mL NH4OH with lots of fuming observed. The reaction was stirred vigorously for a few minutes. The reaction was filtered and the solid was rinsed with CHCl3 (3×100 mL).

Provenance & Evidence