Benzonitrile → HCID 68913860, compound

HRID 1455272Notes

Reaction equation

HRID 1455272 reaction equation
[C:1](#[N:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH2:9].[NH2:10][NH2:11]>C(O)(=O)C>[CH3:4][C:3]1[C:2]([O:9][C:5]2[CH:6]=[CH:7][C:2]([C:1]#[N:8])=[CH:3][CH:4]=2)=[C:7]([CH3:6])[NH:11][N:10]=1

Participants

4

Reactant 2

HCID 7505BenzonitrileHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 68913860HCID 68913860, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The benzonitrile of Preparation 1 (7.2 g, 33 mmol) was dissolved in acetic acid (70 ml). Hydrazine hydrate (1.9 ml, 39.7 mmol) was then added, and the reaction mixture was stirred at room temperature for 1 hour, under nitrogen. It was then concentrated under reduced pressure, and the residue was purified by flash chromatography on silica gel eluting with dichloromethane:ethyl acetate (3:1 then 1:1, by volume) to provide the title compound (4.09 g, 88%) as a pale yellow solid.

Workup

  1. concentrationIt was then concentrated under reduced pressure
  2. customthe residue was purified by flash chromatography on silica gel eluting with dichloromethane:ethyl acetate (3:1

Sources & evidence

ORD record
ord-70baec235eb145ef99621130316b0c91
Source dataset
uspto-grants-2009_01
Patent number
US07482375B2

Reaction notes

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