Hydrochloric Acid → HCID 178450041, compound

Participants

Reaction Steps

A solution of 7-Butoxy-2-hydroxy-3,3-dimethyl-2,3-dihydro-5H-benzo[g]indol-5-one 1-oxide (compound 6 prepared in step (ii) above)(13 mg, 0.036 mmol) in EtOH (2 mL) with conc. HCl in EtOH (0.5 mL) was heated at 60° for 1 h. The yellow solution turned red. When no starting material remained, benzoquinone (39 mg, 0.36 mmol) was added and the mixture was heated 1 h. The solvent was evaporated and the crude product was purified on RP-HPLC. Yield. 12 mg. (24%). 1H NMR (400 MHz, CDCl3) δ 1.00 (tr., 3H), 1.51 (m, 2 H), 1.55 (s, 6 H), 1.82 (m, 2 H), 4.10 (tr., 2H), 7.20 (dd, 1 H), 7.46 (d, 1 H), 7.70 (d, 1 H), 9.62 (br.s, 1 H). MS (EI) m/z 313 (M+).

Provenance & Evidence