Water → HCID 14391136, compound

Participants

Reaction Steps

To a suspension of 11.5 g (0.057 mole) of 5-nitroindole-3-acetonitrile and 1.46 g (0.006 mole) of benzyltriethyl ammonium chloride in 120 ml of 50% (aq.) NaOH, stirred at 0°, was added, dropwise over 1.5 hours, a solution of 8.26 g (0.058 mole) of CH3I in 80 ml of CH2Cl2. The temperature was raised to 25° and the stirring continued for 2 hours. The suspension was then poured into 800 ml of H2O and filtered. The CH2Cl2 layer of the filtrate was taken to dryness in vacuo and the resulting yellow solid combined with the solid from the filtration. The combined solids were washed with H2O, dried and recrystallized from n-BuOH to give 9.35 g (76%) of a yellow solid: m.p. 165°-166°; nmr (d6 -DMSO) δ(TMS) 8.54 (1, d, J=2.5 Hz), 8.16 (1, d of d, Jortho =9 Hz, Jmeta =2.5 Hz), 7.37 (1, d, J=9 Hz), 7.29 (1, S), and 3.86 ppm (5, S, N--CH3 and --CH2 --CN).

Provenance & Evidence