Hydrochloric Acid → HCID 67254174, compound

Participants

Reaction Steps

To a solution of 5-bromo-8-nitro-2-methylisoquinolin-1(2H)-one (Compound 123B, 0.350 g, 1.2 mmol) in ethanol (15 mL) was added iron powder (0.5 g) and 2 N HCl (3 mL). The resulting mixture was heated at reflux for 2 h. TLC (EtOAc/CH2Cl2: 1:9) showed the reaction was complete. After cooled to room temperature, the reaction mixture was filtered, solids washed with ethanol/CH2Cl2 mixture. The combined filtrate was evaporated to dryness, neutralized with aq. Na2CO3 (20 mL), and extracted with EtOAc (3×50 mL). The combined organic layer was washed with water (20 mL), dried and evaporated to give a residue, which was purified by column chromatography on silica gel (EtOAc/CH2Cl2: 1:9)) to afford the desired product as a solid (0.120 g, 39%). 1H NMR (CDCl3, 300 MHz): δ=3.51 (s, 3 H), 6.44 (d, J=7.8 Hz, 1 H), 6.53 (br, 2 H), 6.71 (d, J=7.8 Hz, 1 H), 7.03 (d, J=7.5 Hz, 1 H), 7.49 (d, J=8.7 Hz, 1 H).

Provenance & Evidence