Glutaric anhydride → 5-[(2-Acetylphenyl)amino]-5-oxopentanoic acid

HRID 2297529Notes

Reaction equation

HRID 2297529 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].[C:11]1(=[O:18])[O:17][C:15](=[O:16])[CH2:14][CH2:13][CH2:12]1>C1C=CC=CC=1>[C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:11]([CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[O:18])(=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 7940Glutaric anhydrideHCID 110862'-Aminoacetophenone

Product 1

HCID 183819175-[(2-Acetylphenyl)amino]-5-oxopentanoic acidYield 66.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1-(2-aminophenyl)ethane-1-one (4.00 g) and glutaric anhydride (4.10 g) were dissolved in benzene (30 ml) and the solution was heated to reflux for 3.5 hours, followed by concentration of the mixture. The residue was recrystallized from ethyl acetate to obtain 4.93 g of 4-(N-(2-acetylphenyl)carbamoyl)butanoic acid as colorless plate-like crystals. Yield: 66%.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 3.5 hours
  3. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-4848e64aeb4545f9ae2805d9193980db
Source dataset
uspto-grants-2002_12
Patent number
US06492364B1

Reaction notes

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