Ammonia → 6-Chloropyridazine-3-carboxamide

Reaction equation

[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([O:10]CCCC)=O)=[CH:4][CH:3]=1.[NH3:15]>C1COCC1>[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([NH2:15])=[O:10])=[CH:4][CH:3]=1

Participants

Procedure

A solution of the chloro pyridazine compound from the previous step (51 g, 0.238 mole) in THF (375 ml) was treated with methanolic ammonia (saturated, 80 ml). The reaction was allowed to stand at ambient temperature overnight. The precipitate was filtered and dried to give 6-chloropyridazine-3-carboxamide as a pink solid (18.2 g, 49%). [Further material could be obtained by evaporating the filtrate (at reduced pressure) and treating the residue with THF (100 ml) and methanolic ammonia (40 ml). The product was isolated as before to give a pink solid (17.4 g). Total yield (35.6 g, 95%)].