4-Chlorobenzonitrile → 4-Chlorobenzenehydroxamic acid

HRID 1963004Notes

Reaction equation

HRID 1963004 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#N)=[CH:4][CH:3]=1.[ClH:10].[NH2:11][OH:12].[OH-:13].[Na+]>CCO>[Cl:10][C:2]1[CH:9]=[CH:8][C:5]([C:6]([NH:11][OH:12])=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 121634-ChlorobenzonitrileHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 5871784-Chlorobenzenehydroxamic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-chiorobenzonitrile (0.50 g, 3.60 mmol) in EtOH (10 ml) was added hydroxylamine hydrochloride (0.15 g, 3.60 mmol) and NaOH (2.90 g, 3.60 mmol). The resulting reaction mixture was refluxed for 2 h. After the completion of the reaction (TLC monitoring), the mixture was concentrated, added EtOH and filtered. The filtrate was evaporated in vacuo and used as such for the next step (crude yield 0.50 g, 77%).

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed for 2 h
  3. customAfter the completion of the reaction (TLC monitoring)
  4. concentrationthe mixture was concentrated
  5. additionadded EtOH
  6. filtrationfiltered
  7. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-4a59d33dd24d46bb9250f26d1ac3c8f6
Source dataset
uspto-grants-2013_04
Patent number
US08415383B2

Reaction notes

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