反应详情

Ethyl 4-nitroindole-2-carboxylate (26 g) [prepared according to S. M. Parmerter el. al. J. Amer. Chem. Soc., 1958, 80, 4621], 3,4-dichlorobenzyl chloride (16 ml), potassium carbonate (17 g) and potassium iodide (2 g) in DMF (250 ml) were stirred at 60° C. for 2 hours. The reaction was concentrated in vacuo and the residue partitioned between water and dichloromethane. Iso-hexane was added to the combined organic extracts resulting in crystallisation of the product as yellow needles (39 g. 89%) NMR d (CD3SOCD3) 1.30 (t, 3H), 4.32 (q, 2H), 5.93 (s, 2H), 6.88 (dd, 1H), 7.18 (d, 1H), 7.52 (d, 1H), 7.56 (dd, 1H), 7.78 (s, 1H), 8.17 (m, 2H); M/z (+) 395 (MH+), 393.

1. concentrationThe reaction was concentrated in vacuo
2. customthe residue partitioned between water and dichloromethane
3. additionIso-hexane was added to the combined organic extracts