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

HRID 1629812Notes

Reaction equation

HRID 1629812 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=O)C>[N:1]1([C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=2)[CH2:12][CH2:13][CH2:14][C:15]1=[O:16]

Participants

4

Reactant 2

HCID 9784-Aminobenzoic AcidHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 7731304-(2-Oxopyrrolidin-1-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

19.2 g (140 mmol) 4-amino-benzoic acid are refluxed for 20 hours together with 25.8 ml (180 mmol) ethyl 4-bromobutyrate in 100 ml DMF. After evaporation i. vac. the residue is combined with 100 ml of water and 50 ml petroleum ether and vigorously stirred for 50 minutes. The precipitate is filtered off, recrystallised from ethanol and dried at 80° C.

Workup

  1. customAfter evaporation i
  2. filtrationThe precipitate is filtered off
  3. customrecrystallised from ethanol
  4. customdried at 80° C.

Sources & evidence

ORD record
ord-3346bee8fc5141d39d2bc8a1d78ac717
Source dataset
uspto-grants-2014_07
Patent number
US08791103B2

Reaction notes

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