Hydrazine hydrate (1:1) → 3-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile

HRID 1874786Notes

Reaction equation

HRID 1874786 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]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 594516123-chloro-5-({6-chloro-3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-2-fluorophenyl}oxy)benzonitrile

Product 1

HCID 594513923-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrileYield 822.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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%).

Workup

  1. customThe reaction mixture was placed in an oil bath at 60° C.
  2. stirringthe reaction was stirred for 1 h
  3. customPurification

Sources & evidence

ORD record
ord-83c766cb77554044baf75ba5824d1996
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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