Pyridine → HCID 45480238, compound

Reaction equation

[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=O)[CH:7]=[N:8][NH:9]2)=[CH:4][CH:3]=1.N1C=CC=CC=1.O=P(Cl)(Cl)[Cl:21]>ClC1C=CC=CC=1>[Cl:21][C:6]1[C:5]2[C:10](=[CH:11][C:2]([CH3:1])=[CH:3][CH:4]=2)[N:9]=[N:8][CH:7]=1

Participants

Procedure

7-Methyl-1-H-cinnolin-4-one (1.3 g, 8.1 mmol) is treated with about 80 mL of chlorobenzene and heated until the solid dissolves. The resulting solution is cooled and treated with pyridine (0.16 mL, 2 mmol) and POCl3 (1.13 mL, 12.2 mmol). The solution is heated to reflux for 1 h then concentrated to dryness. The residue is chromatographed (20% ethyl acetate/hexane) to yield the title compound as a tan solid (˜1 g, 5.6 mmol). MS m/z (M+=178); 1H NMR (CDCl3, 300 MHz) δ9.3 (s, 1H), 8.35 (s, 1H), 8.1 (d, 1H), 7.7 (d, 1H), 2.68 (s, 3H).