KlementineJBS
commented
1 year ago 14.02.23
1-napthylamine (1.00 g, 6.98 mmol) was dissolved in hydrochloric acid (3.4 M, 7 mL) and sodium nitrite (629 mg, 9.12 mmol, 1.3 equiv.) dissolved in water (2 mL) was added. The mixture was allowed to stir at 0 C for 15 minutes before sodium azide (628 mg, 9.66 mmol, 1.4 equiv.) dissolved in water (2 mL) was added. The reaction was stirred at 0 C for 1 hour, then diluted with water (5 mL) and extracted with diethyl ether (4 x 30 mL). The resulting dark red solution was washed with sodium bicarbonate (2 x 50 mL) and brine (2 x 50 mL), dried over magnesium sulphate and concentrated under reduced pressure to yield a dark red liquid.
Notes
- Upon addition of nitrite reaction turns from pale purple to dark red/black very rapidly.
-
After 15 minutes stirring a large amount of black sludge was formed, preventing stirring from preceding until the mixture was agitated
-
Reaction was once again stirring slowly due to formation of black sludge when checked after 1 hr
-
TLC indicated completion. (10% ethyl acetate in hexanes)
Link to HIRAC, and master page #171. Original method from J. Batten's PhD thesis, but a similar method is used by Babin et al..
KBS22 Azidation of 1-naphthylamine.docx
Previous attempt is #56
Reaction scheme
Outcome
897 mg (5.15 mmol), 73%