Hydrazine hydrate (1:1) → 4-((1-Methyl-3,5-diphenyl-1H-pyrazol-4-yl)oxy)aniline

反応式

O.NN.[CH3:4][N:5]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:8]([O:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=2)[C:7]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:6]1>[Pd].C(O)C>[NH2:23][C:20]1[CH:19]=[CH:18][C:17]([O:16][C:8]2[C:7]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[N:6][N:5]([CH3:4])[C:9]=2[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:22][CH:21]=1

参加物

実験手順

Hydrazine hydrate (3 ml, 60% solution) is added to a well stirred mixture of 1-methyl-4-(p-nitrophenoxy)-3,5-diphenylpyrazole (2.56 g, 0.0069 mole), 5% Pd on carbon (0.4 g) and absolute ethanol (40 ml). Gas bubbles form immediately and an exotherm (ca. 50° C.) is observed. After the reaction subsides, the reaction mixture is refluxed for 2 hours. The reaction mixture is cooled slightly and filtered to remove the catalyst. The filtrate is stripped in vacuo to give a white solid 2.4 g (100%), m.p. 167° C. to 169° C. Recrystallization from benzene (20 ml) affords a white solid m.p. 167° C. to 168° C.