[H-].[Na+].[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6](Cl)[CH:5]=1.[Cl:12][C:13]1[N:14]=[N:15][C:16](Cl)=[CH:17][CH:18]=1.Cl>CS(C)=O>[Cl:12][C:13]1[N:14]=[N:15][C:16]([O:10][C:7]2[CH:8]=[CH:9][C:4]([NH2:3])=[CH:5][CH:6]=2)=[CH:17][CH:18]=112 g of sodium hydride was added in portions to a stirred solution of 71.8 g of 1A and 25 g of 3,6-dichloropyridazine in 300 ml of dimethyl sulfoxide, the temperature of the mixture being held at 50° C. The mixture then was stirred for one hour and poured into ice water. The mixture was slightly acidified with dilute hydrochloric acid, and was extracted with methylene chloride. The extract was washed with water, dried (magnesium sulfate) and the solvent was evaporated to give 4-(6-chloro-3-pyridazinyloxy)benzeneamine (1B), as a tan solid, mp: 126°-129° C.
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