4-Aminobenzoic Acid → 4-(2-Oxopyrrolidin-1-yl)benzoic acid

HRID 1635550Notes

Reaction equation

HRID 1635550 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.Br[CH2:12][CH2:13][CH2:14][C:15](OCC)=[O:16]>CN(C)C=O.O>[C:6]([C:5]1[CH:9]=[CH:10][C:2]([N:1]2[CH2:12][CH2:13][CH2:14][C:15]2=[O:16])=[CH:3][CH:4]=1)([OH:8])=[O:7]

Participants

5

Reactant 2

HCID 9784-Aminobenzoic AcidHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 7731304-(2-Oxopyrrolidin-1-yl)benzoic acidYield 66.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-aminobenzoic acid (Aldrich, 3.0 g, 21.9 mmol) and ethyl 4-bromobutyrate (Aldrich, 6.4 g, 32.8 mmol) in 20 mL of dimethylformamide was stirred at reflux for 24 h. The solvent was removed under vacuum to give a crude solid which was suspended in 15 mL of water, collected by filtration and dried. The solid was suspended in a small amount of ether (5 mL), filtered and dried to give 3.0 g (66%) of the title compound as a white solid, mp 244-246° C. (ether/ethanol), lit.mp 244-245° C. [Hopff et al. Ger. 859, 007, Sep. 22, 1952; Chem. Abstr. 52 11124h (1958)].

Workup

  1. temperatureat reflux for 24 h
  2. customThe solvent was removed under vacuum
  3. customto give a crude solid which
  4. filtrationcollected by filtration
  5. customdried
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-7c7638e59c7d483ca13447a46b16e3c7
Source dataset
uspto-grants-2003_01
Patent number
US06509359B1

Reaction notes

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