Acetic Acid → 5-Nitroquinoline-8-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

Compound 12A (1.0 g, 5.3 mmol) was dissolved in concentrated H2SO4 (7 mL), cooled to 0° C., and then CrO3 (2.12 g, 21.3 mmol) was added portionwise over 30 min. After the addition, the reaction mixture was warmed to rt and then heated to 80° C. for 1 h. After cooling to rt, the reaction was diluted with water, basified with 15% aqueous NaOH, then reacidified to pH=3 with AcOH, and extracted with EtOAc (4×100 mL). The combined EtOAc extracts were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure to yield the title compound (760 mg, 66%) as a yellow solid. LC/MS m/z 219 [M+H]+.

Provenance & Evidence