Hydrazine hydrate (1:1) → 4-(4-methoxyphenyl)-3-methylisoxazolo[3,4-d]pyridazin-7(6H)-one
Reaction equation
C([O:3][C:4]([C:6]1[C:10]([C:11](=O)[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[C:9]([CH3:21])[O:8][N:7]=1)=O)C.O.[NH2:23][NH2:24]>C(O)C>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([C:11]2[C:10]3[C:6](=[N:7][O:8][C:9]=3[CH3:21])[C:4](=[O:3])[NH:23][N:24]=2)=[CH:13][CH:14]=1Participants
4
Procedure
A solution of 2.47 g of 4-(4-methoxybenzoyl)-5-methylisoxazole-3-carboxylic acid ethyl ester (8.54 mmol) and 0.598 mL of hydrazine monohydrate (12.0 mmol) in 18.4 mL ethanol was stirred at room temperature for 19 hours. The heterogeneous reaction was cooled in an ice bath then filtered off the white solid, washing with cold ethanol then diethyl ether. Dried on under high vacuum to give 2.06 g (92%) of 4-(4-methoxyphenyl)-3-methyl-6 h-isoxazolo[3,4-d]pyridazin-7-one.