Hydrochloric Acid → HCID 18327558, compound

Participants

Reaction Conditions

Reaction Steps

1H-Indole-2-carboxylic acid ethyl ester(1.027 g, 5.4 mmol) was dissoved in 15 ml of dry dimethylformamide and stirred under nitrogen in an ice-bath. Sodium hydride (60% in paraffin oil; 274 mg, 6.85 mmol) was added and the solution stirred at room temperature for 1.5 hours. To the reaction mixture 2-(4-nitrophenyl)ethyl bromide (1.29 g, 5.6 mmol) was added and the solution was stirred overnight. The reaction mixture was heated for 4 hours at 60° C. After completion of the reaction (thin layer chromatography, chloroform/methanol/acetic acid 90:9:1) 20 ml of 2 N hydrochloric acid was added and the reaction mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried with magnesium sulfate, and evaporated to give an orange-red oil. The oily product was taken up in methanol/water (15 ml), and 1.2 g of potassium hydroxide were added. The reaction mixture was stirred overnight to complete the hydrolysis. Workup was achieved by addition of 2 N hydrochloric acid and extraction with ethyl acetate. Washing of the ethyl acetate layer with water, drying with magnesium sulfate, and evaporation in vacuo gave 1(2-(4-nitrophenyl)-ethyl)-1H-indole-2-carboxylic acid. MS: 310.2.

Provenance & Evidence