Hydrochloric Acid → HCID 52913023, compound

Participants

Reaction Steps

2-(2-Nitrophenyl)-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one (Example 427, 0.50 g, 1.1 mmol) was dissolved in methanol (20 mL) and treated with tin(II) chloride dihydrate (1.2 g, 5.4 mmol, 5 equiv) and hydrochloric acid (0.18 mL, 6 M aqueous, 1.1 mmol, 1 equiv). The mixture was placed into a preheated oil bath at 45° C. for 2 hours, cooled to ambient temperature and the pH of the mixture was brought to ˜pH 7 by addition of sodium hydroxide (1 N aqueous). The mixture was extracted with ethyl acetate (2×100 mL) and the combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo, providing the titled compound: 1H-NMR (400 MHz, d6-DMSO) δ 9.17 (1H, s), 8.46 (1H, d, J=2.3 Hz), 8.23 (1H, d, J=7.8 Hz), 7.83 (2H, d, J=8.5 Hz), 7.79 (1H, d, J=8.8 Hz), 7.72 (1H, br s), 7.62 (1H, t, J=7.4 Hz), 7.54 (1H, t, J=7.5 Hz), 7.46 (2H, d, J=8.6 Hz), 7.33 (1H, d, J=7.6 Hz), 7.10 (1H, t, J=7.7 Hz), 6.87 (1H, d, J=8.1 Hz), 6.70 (1H, t, J=7.5 Hz), 6.53 (1H, br m), 5.80 (1H, br s), 5.76 (2H, s), 5.19 (1H, br s) ppm; high resolution mass spectrometry (ES+) m/z 433.0 [(M+H)+; calculated for C26H21N6O: 433.2].

Provenance & Evidence