Sodium Hydroxide → HCID 89783435, compound

Participants

Reaction Steps

Methyl 8-(4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl)quinoline-2-carboxylate (0.84 g, 2.62 mmol) was dissolved in THF (25 mL), NaOH 1.00 N (2.62 mL, 2.62 mmol) was added, and the resulting solution was stirred at RT for 3 h, then at 40° C. for 2 h. The reaction mixture was then concentrated in vacuo the pH was adjusted to <4 using 5 N HCl. A precipitate formed and was isolated by filtration to give 8-(4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl)quinoline-2-carboxylic acid (647 mg, 2.11 mmol, 80% yield) as a dark-brown solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 13.71 (br. s., 1H), 12.72 (br. s., 1H), 8.59 (d, J=8.4 Hz, 1H), 8.26 (d, J=7.4 Hz, 1H), 8.16 (d, J=8.6 Hz, 1H), 7.89 (d, J=8.0 Hz, 1H), 7.72 (t, J=7.7 Hz, 1H), 7.30-7.34 (m, 1H), 7.04 (br. s., 1H), 3.46 (t, J=6.5 Hz, 2H), 2.90 (t, J=6.7 Hz, 2H). m/z (ESI, +ve ion) 308.0 (M+H)+.

Provenance & Evidence