Potassium Hydroxide → HCID 18407219, compound

HRID 2271213Notes

Reaction equation

HRID 2271213 reaction equation
[OH-].[K+].[C:3]([N:6]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]([O:29]C)=[O:28])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:5])[CH3:4]>CO>[C:3]([N:6]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]([OH:29])=[O:28])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:5])[CH3:4]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 9842567HCID 9842567, compound

Product 1

HCID 18407219HCID 18407219, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 23 ml of methanol and 3.6 ml of 2 N aqueous potassium hydroxide solution was added 2.26 g of N-acetyl-N-(2-methoxycarbonylbenzyl)-2-phenoxyaniline synthesized in the same manner as in Example 2, followed by stirring at 60° C. for an hour. The reaction mixture was concentrated under reduced pressure, water was added to the residue, and the mixture was made acidic with 2 N hydrochloric acid and extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; ethyl acetate-hexane=1:1) to give 2.01 g of N-acetyl-N-(2-carboxybenzyl)-2-phenoxyaniline as an oil.

Workup

  1. customsynthesized in the same manner as in Example 2
  2. concentrationThe reaction mixture was concentrated under reduced pressure, water
  3. additionwas added to the residue
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter removal of the drying agent
  8. filtrationby filtration
  9. concentrationthe solvent was concentrated under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (eluent; ethyl acetate-hexane=1:1)

Sources & evidence

ORD record
ord-658239c1848141e399ab359e5b666f91
Source dataset
uspto-grants-2001_12
Patent number
US06333358B1

Reaction notes

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