Ethanol → Trifluoromethoxy phenyl-N-hydroxy-benzamide

HRID 538564

Reaction equation

HRID 538564 reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7](C#N)=[CH:6][CH:5]=1.Cl.[NH2:15][OH:16].[OH-].[Na+].C[CH2:20][OH:21]>>[F:13][C:2]([F:1])([F:12])[O:3][C:4]1[C:5]([C:4]2[CH:11]=[CH:10][CH:7]=[CH:6][CH:5]=2)=[C:6]([CH:7]=[CH:10][CH:11]=1)[C:20]([NH:15][OH:16])=[O:21]

Participants

5

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 676214-(Trifluoromethoxy)benzonitrileHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 86643274Trifluoromethoxy phenyl-N-hydroxy-benzamide

Procedure

To a solution of 4-Trifluoromethoxybenzonitrile (1.0 g, 5.0 mmol) in EtOH (20 mL) was added hydroxylamine hydrochloride (0.365 g, 5.0 mmol) and NaOH (0.212 g, 5.0 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-07e7c7730ae3400bb48e061324818fb3
Source dataset
uspto-grants-2014_10
Patent number
US08865736B2

Linked notes

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