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

HRID 1874764Notes

Reaction equation

HRID 1874764 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

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 594515253-chloro-5-({2-chloro-5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}oxy)benzonitrile

Product 1

HCID 594514053-{[5-(Aminomethyl)-2-chlorophenyl]oxy}-5-chlorobenzonitrileYield 74.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Chloro-5-({2-chloro-5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}oxy)benzonitrile (1.0 g, 2.3 mmol) was dissolved in methanol (25 mL) and hydrazine monohydrate (0.3 mL, 5.9 mmol) was added. The reaction was stirred for 4 h. Additional hydrazine monohydrate (0.3 mL, 5.9 mmol) was added and stirred overnight. The solvent was evaporated and the crude product was purified by column chromatography (hexane/EtOAc) to afford the title compound (0.5 g, 72%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 7.77 (t, 1H), 7.53 (d, 1H), 7.40 (dd, 1H), 7.32 (t, 1H), 7.19-7.29 (m, 2H), 3.68 (s, 2H), 1.89 (br. s., 2H). MS: m/z 292.9 (M+1).

Workup

  1. stirringstirred overnight
  2. customThe solvent was evaporated
  3. customthe crude product was purified by column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-8f7e3ea697ab46478574426ac681d5fe
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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