Hydrazine hydrate (1:1) → tert-Butyl 2-(4-(5-(4-chlorophenyl)-1H-pyrazol-3-yl)phenyl)morpholine-4-carboxylate
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH:18]3[O:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19]3)=[CH:14][CH:13]=2)=O)=[CH:4][CH:3]=1.O.[NH2:33][NH2:34]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:34][N:33]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([CH:18]4[O:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19]4)=[CH:14][CH:13]=3)[CH:9]=2)=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of tert-butyl 2-(4-(3-(4-chlorophenyl)-3-oxopropanoyl)phenyl)morpholine-4-carboxylate (210 mg, 0.473 mmol) and hydrazine hydrate (35.5 mg, 0.70 mmol) in ethanol (3.5 ml) was heated to reflux with stirring overnight. The clear yellow solution was evaporated under reduced pressure, water was added and ethyl acetate. The organic layer was separated, the aqueous layer was extracted again with ethyl acetate. The combined organic layers were dried over MgSO4 and evaporated. The crude material was purified by flash chromatography (10 g silica gel, 10 to 50% ethyl acetate in heptane) to yield a white solid (208 mg, 89%). MS (ISP neg): 438.3 ([{35Cl}M−H]+), 440.4 ([{37Cl}M−H]+).