Ethanol → Trifluoromethoxy phenyl-N-hydroxy-benzamide

HRID 415639Notes

Reaction equation

HRID 415639 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-c8d553a8b896403caea3eda8a9e78ae2
Source dataset
uspto-grants-2012_01
Patent number
US08088791B2

Reaction notes

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