Acetic Acid → Methyl indole-6-carboxylate

Participants

Reaction Conditions

Reaction Steps

Into a reaction flask were introduced 176.4 g of iron powder, 43.5 g of acetic acid, 71.2 g of water and 273.3 g of toluene. The content of the flask was heated to 80° C. Then, a solution of 131.8 g of methyl 4-methyl-3-nitrobenzoate in 110.4 g of DMF was dropwise added into the above-mentioned mixed solution over a period of about one hour, after which the resulting mixture was stirred for an additional 4 hours at 80° C. After cooling the reaction mixture, the solid material was removed by filtration. The filtrate was washed with 5% aqueous solution of NaOH, and washed with 5% aqueous solution of hydrochloric acid and water, and then the toluene was distilled off to obtain a brown-colored solid product. Then, 164.3 g of cyclohexane was added to dissolve the solid product at about 80° C. The resulting solution was cooled to room temperature, and the deposited crystalline material was collected by filtration and dried to obtain 73.8 g (yield 80.0%) of methyl indole-6-carboxylate monomer.

Provenance & Evidence