Methyl iodide → 1H-Indole, 2,3-dihydro-1-methyl-5-nitro-

Participants

Reaction Conditions

Reaction Steps

25 ml of anhydrous DMF is introduced into a 150 ml three-necked flask, under an inert atmosphere, followed by 0.84 g (21 mmol) of 60% NaH. The reaction mixture is cooled down using an ice bath before the dropwise addition of a solution of 3.28 g (20 mmol) of 5-nitroindoline in 5 ml of anhydrous DMF. At the end of the addition, agitation is maintained for 1 hour at 23° C., before introducing dropwise a solution of 1.31 ml (21 mmol) of MeI in 5 ml of anhydrous DMF. Agitation is continued for 15 hours at 23° C. The reaction is finally neutralized, at 0° C., with 20 ml of a saturated solution of NH4Cl. The reaction mixture is then diluted with 20 ml of water and 50 ml of AcOEt. After decanting, the organic phase is washed successively with 20 ml of water then 20 ml of salt water, dried over magnesium sulphate, filtered and concentrated under vacuum. A dark yellow powder is obtained.

Provenance & Evidence