Hydroxyamine hydrochloride → 7-Bromo-9,9-diethylfluorene-2-carbonitrile

Participants

Reaction Steps

An alternate, but less satisfactory synthesis was conducted as follows: A mixture of 7-bromo-9,9-diethylfluorene-2-carboxaldehyde (3.29 g, 10.0 mmol), hydroxylamine hydrochloride (0.9 g, 10.0 mmol), and formic acid (15 ml) was held at reflux for 2 hours, cooled, and filtered. The filtrate was worked up by extraction into toluene, washing the extract with water and bicarbonate solution, drying, and concentrating. The residue was combined with the formic acid-insoluble solids and chromatographed over silica gel. Obtained were the desired nitrile product, 1.58 g (49%), m.p. 85-87° C., mass spec (m/z): 325, 327 (M+); the amide byproduct, 0.42 g (12%), m.p. 179-184° C., mass spec (m/z): 343, 345 (M+); and the oxime byproduct, m.p. 104-107° C., 0.17 g (5%), mass spec (m/z): 343 (M+).

Provenance & Evidence