Hydrochloric Acid → HCID 66605036, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 7-isopropyl 4-methyl 2-phenyl-5H-pyrido[3,2-b]indole-4,7-dicarboxylate (380 mg, 0.978 mmol) in a mixture of THF (5.6 mL), MeOH (1.9 mL) and 1 N aqueous sodium hydroxide solution (2.0 mL, 2.0 mmol) was stirred at 25° C. for 15 min. The reaction was treated with 1 N aqueous HCl (0.52 mL) and the organic solvents were removed. The residue was diluted with water and acidified to about pH 3.0 with 1 N aqueous HCl to give an yellow gel-like precipitate. This was chilled in an ice bath and the precipitate was collected by filtration, washed with water and dried to leave impure 7-(isopropoxycarbonyl)-2-phenyl-5H-pyrido[3,2-b]indole-4-carboxylic acid (395 mg). MS (ESI) m/z 375.09 (M+H). 1H NMR (500 MHz, DMSO-d6) δ ppm 11.88 (1H, s), 8.35-8.50 (3H, m), 8.25 (2H, d, J=7.94 Hz), 7.83-7.96 (1H, m), 7.56 (2H, t, J=7.78 Hz), 7.46 (1H, t, J=7.17 Hz), 5.22 (1H, quin, J=6.26 Hz), 1.40 (6H, d, J=6.10 Hz).

Provenance & Evidence