Glutaric anhydride → 4-(N-(2-formylphenyl)carbamoyl)butanoic acid

HRID 2297521Notes

Reaction equation

HRID 2297521 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C:10]1(=[O:17])[O:16][C:14](=[O:15])[CH2:13][CH2:12][CH2:11]1>C1C=CC=CC=1>[CH:4]([C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[NH:1][C:10]([CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[O:17])=[O:5]

Participants

4

Reactant 2

HCID 7940Glutaric anhydrideHCID 682552-Aminobenzaldehyde

Product 1

HCID 183819544-(N-(2-formylphenyl)carbamoyl)butanoic acidYield 93%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-aminobenzaldehyde (2.87 g) and glutaric anhydride (3.26 g) were dissolved in benzene (60 ml) and the mixture was heated to reflux for 10.5 hours. Benzene was removed and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1- ethyl acetate) to obtain 5.12 g of 4-(N-(2-formylphenyl)carbamoyl)butanoic acid. Yield: 93%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 10.5 hours
  3. customBenzene was removed
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1- ethyl acetate)

Sources & evidence

ORD record
ord-1a75c3bfb9164c90aef14835fb5ab249
Source dataset
uspto-grants-2002_12
Patent number
US06492364B1

Reaction notes

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