4-Aminophenol → 1-(4-hydroxyphenyl)pyrrolidin-2-one

HRID 1173427Notes

Reaction equation

HRID 1173427 reaction equation
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([OH:8])[CH:2]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:16][CH2:17][CH2:18][C:19](Cl)=[O:20].CN(C=O)C>CC#N.O>[OH:8][C:3]1[CH:4]=[CH:5][C:6]([N:7]2[CH2:16][CH2:17][CH2:18][C:19]2=[O:20])=[CH:1][CH:2]=1

Participants

7

Reactant 4

HCID 4034-AminophenolHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 783704-Chlorobutyryl chloride

Product 1

HCID 7855861-(4-hydroxyphenyl)pyrrolidin-2-oneYield 19.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of p-aminophenol (0.545 g, 5.00 mmol) in dry MeCN (5 mL) at 0° C. was added K2CO3 (1.38 g, 10.0 mmol), followed by dropwise addition of 4-chlorobutanoyl chloride (0.56 mL, 5.0 mmol). The mixture was stirred at rt for 40 min and then brought to reflux. Dry DMF (5 mL) was added after 90 min and heating was continued for an additional 2 h. The mixture was cooled, poured into water, and extracted with EtOAc (×8). Combined organics were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording 0.171 g of the title compound as a colorless solid: MS (APCI) m/z 177 (M+).

Workup

  1. temperatureto reflux
  2. temperatureheating
  3. waitwas continued for an additional 2 h
  4. temperatureThe mixture was cooled
  5. extractionextracted with EtOAc (×8)
  6. washCombined organics were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-a1bc74e7e76648dbaa7da23bb8203476
Source dataset
uspto-grants-2010_11
Patent number
US07834063B2

Reaction notes

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