Hydrazine hydrate (1:1) → 3-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[C:16]([Cl:17])=[CH:15][CH:14]=[C:13]([CH2:18][N:19]3C(=O)C4C(=CC=CC=4)C3=O)[C:12]=2[F:30])[CH:9]=1)[C:5]#[N:6].O.NN>CO>[NH2:19][CH2:18][C:13]1[C:12]([F:30])=[C:11]([O:10][C:8]2[CH:7]=[C:4]([CH:3]=[C:2]([Cl:1])[CH:9]=2)[C:5]#[N:6])[C:16]([Cl:17])=[CH:15][CH:14]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
3-Chloro-5-({6-chloro-3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-2-fluorophenyl}oxy)benzonitrile (1.9 g, 4.3 mmol) was dissolved in MeOH (50 mL) and hydrazine monohydrate (0.63 mL, 12.9 mmol) was added. The reaction mixture was placed in an oil bath at 60° C. and stirred for 2 h. Another portion of hydrazine monohydrate (0.63 mL, 12.9 mmol) was added and the reaction was stirred for 1 h. Purification was accomplished by column chromatography (CH2Cl2/MeOH) to afford the title compound (11 g, 82%).