Toluene → Ethyl 5-nitro-1-propyl-1H-indole-2-carboxylate

Participants

Reaction Steps

To 3.69 g (15.75 mmol) of commercial ethyl 5-Nitro-2-carboxy-indole dissolved in 35 mL of DMSO was added 2.01 g (31.5 mmol) of KOH. The reaction was stirred vigourously for 30 mins., at which time 2.86 mL (31.5 mmol) of propyl bromide was added. After 4 hours an additional 5 mL DMSO was added and the reaction was reacted overnight. 1 mL 5% aqueous NH4Cl was added and poured into toluene (150 mL) and washed with saturated NaHCO3 (100 mL). The aqueous layer was extracted twice with toluene (75 mL each) and the combined organic layers washed with brine (100 mL), dried over Na2SO4 and concentrated. The product was dissolved in 100 mL dioxane and freeze-dried to give 4.15 g (15.1 mmol, 95%) of 93.

Provenance & Evidence