Methanol → 3H-Indole, 2,3,3-trimethyl-5-nitro-

Participants

Reaction Conditions

Reaction Steps

Sodium nitrate (3.84 g, 45.2 mmol) was dissolved in concentrated sulphuric acid (100 ml). After cooling in ice, this solution was added to a solution of 2,3,3-trimethylindole (6.65 g, 41 .8 mmol) in concentrated sulphuric acid (100 ml) such that the temperature was maintained in the range 0-5° C. The reaction was stirred at 0-5° C. for 90 minutes after completing the addition, then allowed to warm to room temperature and stirred for a further 16 hours. The mixture was poured onto ice (200 g) then made basic by the addition of 50% aqueous sodium hydroxide solution to pH12 (pH paper). The crude product was collected by filtration and washed with water until the washings were neutral (˜1000 ml). The off-yellow solid was dried at the pump, dissolved in ethyl acetate (250 ml) and dried further (MgSO4). The solution was filtered and the red filtrate was rotary evaporated to dryness. The solid was dissolved in chloroform:ethyl acetate (95:5, 30 ml) and purified by silica flash chromatography. This gave a dark yellow solid, 5.12 g, 25 mmol, 60% yield. UV analysis (methanol) showed a single peak with λmax=300 nm. Mass spectrometry (MALDI-TOF with a gentisic acid matrix) gave m/z=203.8 (for C11H12N2O2=204.23). 1H NMR:δ=1.97 (s, 6H), 2.95 (s, 3H), 8.58 (d, J=10 Hz, 1H), 8.70 (s, 1H), 8.78 (d, J=10 Hz, 1H).

Provenance & Evidence