Methyl iodide → 3-Cyanomethyl-4-chloro-5-benzyloxyindole

Participants

Reaction Steps

Potassium cyanide (7.36 g, 113 retool) was added to a solution of 3-dimethylaminomethyl-4-chloro-5-benzyloxy-indole (9.30 g, 29.5 mmol) in sieve-dried DMF (150 ml). Methyl iodide (17.2 g, 121 mmol) was added dropwise, while stirring over 15 minutes, and stirring was continued for a further hour. The mixture was poured into 10% aqueous sodium sulphate and extracted with diethyl ether. The combined extracts were dried (Na2SO4) and evaporated to dryness leaving an oil which crystallised. Recrystallisation from methanol gave 3-cyanomethyl-4-chloro-5-benzyloxyindole (5.56 g), m.p. 130°-2° C.

Provenance & Evidence