Acetic Anhydride → 4-Nitrothiophene-2-carbonitrile

Participants

Reaction Conditions

Reaction Steps

Acetic anhydride (1.2 mL) was added to a mixture of aldehyde 1 (314.3 mg, 2.00 mmol) and hydroxylamine hydrochloride (277.6 mg, 4.00 mmol) in pyridine (1.5 mL) pre-heated at 95° C. according to the procedure of M. Bobosikova et al. (J. Chem. Soc., Perkin Trans. I, 2001, 680-689). After 2 h at 95° C. the mixture was cooled and poured over ice and the precipitate was filtered out and allowed to air dry. Nitrile 2 was obtained in 68% yield as beige solid 1H NMR (CDCl3) δ(ppm): 8.51 (s, 1H), 8.14 (s, 1H).

Provenance & Evidence