Hydrazine hydrate (1:1) → HCID 53328542, compound
Reaction equation
O.NN.[Br:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:6]=1[CH2:15][N:16]1C(=O)C2C(=CC=CC=2)C1=O>C(#N)C>[Br:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:6]=1[CH2:15][NH2:16]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
4.4 mL of hydrazine hydrate was added to 2-[(2-bromo-3-methyl-5-nitrophenyl)methyl]-2,3-dihydro-1H-isoindole-1,3-dione (4.4 g, 11.7 mmol) in 220 mL of acetonitrile. The mixture was stirred under reflux overnight and then was allowed to cool to room temperature. The phtalhydrazide side product was remove by filtration and washed with 100 mL portions of acetonitrile. The combined acetonitrile filtrates were evaporated and the residue was partitioned between water and ethyl acetate. The organic layer was extracted with two 100 mL portions of aqueous HCl 1 M. The combined acidic aqueous layers were basified to pH=10 with solid potassium hydroxide and then extracted with ethyl acetate. The organic layer was dried over Na2SO4 filtered and evaporated to yield expected compound as an orange solid (2.15 g, 75% yield). m/z (ESI) 245.0 [M+H]+;