Hydroxylamine → 4-chloro-N'-hydroxybenzenecarboximidamide

HRID 558003Notes

Reaction equation

HRID 558003 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[NH2:10][OH:11]>CCO>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6](=[N:10][OH:11])[NH2:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 121634-Chlorobenzonitrile

Product 1

HCID 2246504-chloro-N'-hydroxybenzenecarboximidamideYield 76.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-chlorobenzonitrile (1 g, 7.23 mmol) and hydroxylamine (50% in water, 0.67 cm3, 10.9 mmol, 1.5 eq) in EtOH (12.5 cm3) was stirred under reflux for 48 hours. The solvent was removed under reduced pressure and the residue was washed with CH2Cl2 (10 cm3) to give the product 4-chloro-N′-hydroxybenzimidamide (0.94 g, 76%) as a white solid, mp 133-135° C.

Workup

  1. temperatureunder reflux for 48 hours
  2. customThe solvent was removed under reduced pressure
  3. washthe residue was washed with CH2Cl2 (10 cm3)

Sources & evidence

ORD record
ord-b295f0a1952f4bf7a367c2f0846d0f21
Source dataset
uspto-grants-2011_11
Patent number
US08062429B2

Reaction notes

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