4-Chlorobenzonitrile → 4-Chlorobenzenehydroxamic acid

HRID 415628Notes

Reaction equation

HRID 415628 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-chlorobenzonitrile (10.0 g, 73.0 mmol) in EtOH (250 mL) was added hydroxylamine hydrochloride (5.03 g, 73.0 mmol) and NaOH (2.90 g, 73.0 mmol). The resulting reaction mixture was refluxed for 15 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 12.0 g, 66%).

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed for 15 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-4c70460e1a2549e3a086f903a06adcb5
Source dataset
uspto-grants-2012_01
Patent number
US08088791B2

Reaction notes

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