Potassium Hydroxide → 1-(4-Aminophenyl)propan-1-one O-(4-(trifluoromethyl)benzyl)oxime

HRID 68315Notes

Reaction equation

HRID 68315 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:24]=[CH:23][C:6]([CH2:7][O:8][N:9]=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([NH:19]C(=O)C)=[CH:15][CH:14]=2)[CH2:11][CH3:12])=[CH:5][CH:4]=1.[OH-].[K+]>C(O)C.O>[F:1][C:2]([F:25])([F:26])[C:3]1[CH:24]=[CH:23][C:6]([CH2:7][O:8][N:9]=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)[CH2:11][CH3:12])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86699622N-(4-(1-(((4-(Trifluoromethyl)benzyl)oxy)imino)propyl)phenyl)acetamide

Product 1

HCID 866996241-(4-Aminophenyl)propan-1-one O-(4-(trifluoromethyl)benzyl)oximeYield 84.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of the product of step 1 (10 g, 0.0275 moles) in ethanol (70 ml), a solution of potassium hydroxide (6.15 g, 0.1098 moles) in water (30 ml) was added and the reaction mixture was stirred at 80-90° C. for 36 hours. The reaction mixture was poured into ice cold water and extracted by dichloromethane. The combined dichloromethane extract was washed with water and brine, dried over sodium sulphate and evapourated under reduced pressure to yield 7.5 gm (84%) of product as liquid.

Workup

  1. additionThe reaction mixture was poured into ice cold water
  2. extractionextracted by dichloromethane
  3. extractionThe combined dichloromethane extract
  4. washwas washed with water and brine
  5. dry with materialdried over sodium sulphate

Sources & evidence

ORD record
ord-3ecaf34750d7422aa52c11d87cfcf54a
Source dataset
uspto-grants-2014_09
Patent number
US08822414B2

Reaction notes

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