反应详情

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+).

1. customAn alternate, but less satisfactory synthesis
2. temperatureat reflux for 2 hours
3. temperaturecooled
4. filtrationfiltered
5. extractionThe filtrate was worked up by extraction into toluene
6. washwashing the
7. extractionextract with water and bicarbonate solution
8. customdrying
9. concentrationconcentrating
10. customchromatographed over silica gel
11. customObtained