Nitric Acid → HCID 69068910, compound

Participants

Reaction Steps

To a solution of N-(3,3-diethyl-1-isopropyl-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (10.4 g, 36.06 mmol) in conc. sulfuric acid (50 ml) was added slowly a mixture of nitric acid (65%, 3.84 g, 2.72 ml, 39.67 mmol) and conc. sulfuric acid (10 ml) at 0° C. After 2 h at room temperature the mixture was poured into ice water. The precipitate was filtered off, washed with water and dried. The crude material was purified by silica gel chromatography (isohexane/ethyl acetate 1:1) to yield 2.2 g N-(3,3-diethyl-1-isopropyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (6.60 mmol, 18%) besides undesired N-(3,3-diethyl-1-isopropyl-7-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (5.5 g).

Provenance & Evidence