Water → N-hydroxyacetyl-N-(2-methoxybenzyl)-2-phenoxyaniline

HRID 1016578Notes

Reaction equation

HRID 1016578 reaction equation
C([O:4][CH2:5][C:6]([N:8]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[O:29][CH3:30])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:7])(=O)C.C(=O)([O-])[O-].[K+].[K+].O>CO>[OH:4][CH2:5][C:6]([N:8]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[O:29][CH3:30])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:7]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 18407208N-acetoxyacetyl-N-(2-methoxybenzyl)-2-phenoxyaniline

Product 1

HCID 18407186N-hydroxyacetyl-N-(2-methoxybenzyl)-2-phenoxyanilineYield 95.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

In 6 ml of methanol was dissolved 525 mg of N-acetoxyacetyl-N-(2-methoxybenzyl)-2-phenoxyaniline, and then 537 mg of potassium carbonate was added, followed by stirring at 50° C. for 7 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with 5% hydrochloric acid, a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, 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=1:3) and allowed to stand at room temperature to give 450 mg of N-hydroxyacetyl-N-(2-methoxybenzyl)-2-phenoxyaniline as crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with 5% hydrochloric acid
  3. dry with materiala saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate
  4. customAfter removal of the drying agent
  5. filtrationby filtration
  6. concentrationthe solvent was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluent; ethyl acetate−hexane=1:3)
  8. customto stand at room temperature

Sources & evidence

ORD record
ord-2f824a14dcf8469fb49550af5c97bd34
Source dataset
uspto-grants-2002_11
Patent number
US06476056B2

Reaction notes

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