Hydrazine hydrate (1:1) → 3-{[5-(Aminomethyl)-2-chlorophenyl]oxy}-5-chlorobenzonitrile

HRID 1874765Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[CH:16]=[C:15]([CH2:17][N:18]3C(=O)C4C(=CC=CC=4)C3=O)[CH:14]=[CH:13][C:12]=2[Cl:29])[CH:9]=1)[C:5]#[N:6].O.NN>CO>[NH2:18][CH2:17][C:15]1[CH:14]=[CH:13][C:12]([Cl:29])=[C:11]([O:10][C:8]2[CH:7]=[C:4]([CH:3]=[C:2]([Cl:1])[CH:9]=2)[C:5]#[N:6])[CH:16]=1

Participants

Conditions

Temperature: 60 °C

Procedure

3-chloro-5-({2-chloro-5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}oxy)benzonitrile (0.40 g, 0.94 mmol) and hydrazine monohydrate (0.11 mL, 2.3 mmol) dissolved in methanol (10 mL). The reaction was stirred at 60° C. for 1.5 h. The solvent was evaporated and the crude product was purified by column chromatography (hexane/EtOAc) to afford the title compound (0.26 g, 94%) as a solid.

Workup

customThe solvent was evaporated
customthe crude product was purified by column chromatography (hexane/EtOAc)

Sources & evidence

ORD record: ord-0ea6195d033e48b691401560c4623e59
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304419B2

Reaction notes

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