Nitric Acid → HCID 22605917, compound

Participants

Reaction Conditions

Reaction Steps

With efficient ice bath cooling 2-bromo-5,6,7,8-tetrahydro-quinoline 1-oxide (8.0 g, 35 mmol) (S. Zimmermann et al., J. Am. Chem. Soc., 1991, 113, 183) was treated with conc. H2SO4 (65 ml), followed by conc. HNO3 (10 ml). The resulting mixture was heated to 90° C. for 90 min, cooled and poured on crushed ice (200 g). NaOH (28%) was added to reach pH 7 and the aqueous phase extracted with AcOEt. The organic phase was dried (Na2SO4) and concentrated to yield 7.9 g (83%) of the title compound as a yellow oil. MS: m/e=272 (M+).

Provenance & Evidence