Nitric Acid → HCID 178526430, compound

Participants

Reaction Steps

To a suspension of quindolinium hydrochloride [(3.2 g, 1.25 mmol; obtained by acidification of quindoline (example 2) with HCl)], in glacial acetic acid (100 mL) was added dropwise at 0° C. HNO3 (d 1.54, 50 mL). The reaction mixture was stirred at room temperature for 24 hours and poured into ice. The resulting precipitate was collected and washed with a saturated solution of NaHSO4, water and dried to afford 2.4 g 72.5%) of an orange solid. TLC (silica gel, EtOAc-hexane, 1:1) showed two major spots with Rf 0.56 and Rf 0.30. Separation of 1 g of this mixture by LPLC, eluting with EtOAc-hexane (1:3), afforded 290 mg of 6-nitroquindoline (Rf 0.56) and 600 mg of 8-nitroquindoline. The structures of the two compounds were determined by COSY, HMQC, and HMBC 2D-NMR.

Provenance & Evidence