Pyridine → HCID 69663720, compound

Participants

Reaction Steps

The above azide (from Example 6)(21.67 g, 61.16 mmol) dissolved in DMF (400 mL) and THF (500 mL) was degassed with nitrogen for 30 minutes whereupon 10% Pd/C (4.74 g, 4.4 mmols) was added and the reaction hydrogenated on a Parr apparatus (60 psi of hydrogen) for 14 hr. The reaction mixture was removed from the Parr apparatus and placed under a nitrogen atmosphere whereupon pyridine (5.44 mL, 67.3 mmols) and acetic anhydride (6.35 mL, 67.3 mmols) were added. After stirring for 1 hr the reaction mixture was filtered through a pad of Celite, washing thoroughly with methanol and then copious amounts of 50% MeOH/CH2Cl2 (ca. 2 L). The filtrate was evaporated to afford the crude acetamide in DMF. The mixture was slowly added to water (2 L) and the ppt collected on a filter, washed with water (5×400 mL) and dried in a vac oven (50° C.) to provide the acetamide as an analytically pure white solid (14.2 g, 63% yield). The combined filtrates were extracted with methylene chloride (5×200 mL), dried over Na2SO4 and concentrated. Water was added to the residue and the resulting ppt was filtered off and dried in a vac oven (50° C.) to afford a second crop of the acetamide as a light tan, fluffy solid (5.61 g, 25%). For the analytically pure material Mp=229-230° C., decomp. MS (M+1)=371 m/z.

Provenance & Evidence