Hydrochloric Acid → HCID 19760337, compound

Participants

Reaction Steps

4,7-Dichloroquinoline (50 g, 252 mmol) and 4-aminobenzaldehyde (30.6 g, 252 mmol) are stirred in 300 mL of methanol and treated with 126 mL of 2 N HCl. The mixture is boiled on a hot plate and after ~15 minutes, a thick yellow precipitate forms. The heating is continued at a low setting for 3 hours at which point the mixture is allowed to cool to room temperature. The yellow solid is filtered, washed with cold methanol, then ether and dried in vacuo at 60° C. for three days affording 64.65 g (203 mmol, 80% yield) of product: 1H NMR (Me2SO-d6, 300 MHz) δ11.4 (br s, 1H), 10.06 (s, 1H), 8.95 (d,J=9.2 Hz, 1H), 8.65 (d,J=6.9 Hz, 1H), 8.24 (d,J=2.1 Hz, 1H), 8.09 (d,J=8.5 Hz, 2H), 7.92 (d of d,J=2.0, 9.2 Hz, 1H), 7.76 (d,J=8.5 Hz, 2H), 7.13 (d,J=7.0 Hz, 1H).

Provenance & Evidence