Hydrochloric Acid →

Participants

Reaction Steps

Compound C6 (100 mg, 0.28 mmol) was dissolved in EtOH (10 mL) and H2O (5 mL) by heating. 4-Chloroquinoline (60 mg, 0.36 mmol) and 3 drops of c.HCl were added, and the mixture refluxed for 18 h (until TLC with the top phase of 5:4:1 mixture of n-BuOH:H2O:CH3CO2H showed complete consumption of starting amine). The reaction mixture was then diluted with EtOAc, boiled for a few minutes and then allowed to cool to room temperature. The resulting precipitate was filtered and crystallized from MeOH/EtOAc to give Cpd. C (64 mg, 63%); mp (MeOH, EtOAc)>300° C.; 1H NMR [(CD3)2SO] δ14.49 (br, 1 H, N+H), 11.01 (s, 1 H, NH), 11.78 (br, 1 H, NH), 10.64 (s, 1 H, NH), 8.77 (d, J=8.5 Hz, 1 H, ArH), 8.57 (d, J=6.5 Hz, 1 H, ArH), 8.32 (d, J=7.5 Hz, 2H, ArH), 8.06-7.92 (m, 6 H, ArH), 7.53 (t, J=7.7 Hz, 1 H, ArH), 7.70-7.65 (m, 1 H, ArH), 7.48 (d, J=8.8 Hz, 2 H, ArH), 7.29 (d, J=7.5 Hz, 2 H, ArH), 6.79 (d, J=6.8 Hz, 1 H, ArH), 3.98 (s, 3 H, N+CH3).

Provenance & Evidence