Ammonia → HCID 69476210, compound

Participants

Reaction Steps

A solution of 20.0 g (80.2 mmol) of (26) and 8.4 ml (87 mmol) of 3-fluoroaniline (27a) in 65 ml of acetic acid was cooled with a cold water bath. 10.7 ml (80.2 mmol) of trimethylsilylcyanide were added dropwise over a period of 10 min. maintaining the temperature below 40° C. The mixture was stirred for 2 h at room temperature and poured into a mixture of aqueous ammonia (80 ml) and ice (80 g). The pH was adjusted to 10 with concentrated NH3. The mixture was extracted with chloroform (3×200 ml). The combined organic layers were dried over Na2SO4 and concentrated in vacuo to give 40.0 g of crude product, which was purified by column chromatography (SiO2, heptane:EtOAc, 1:1) to give 28.7 g (77.7 mmol, 97%) of (28a). It is also possible to use crude product in the next step without purification.

Provenance & Evidence