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

HRID 2222465Notes

Reaction equation

HRID 2222465 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-7cc7c0e86a56464ba03eaf616328d80c
Source dataset
uspto-grants-2008_05
Patent number
US07371743B2

Reaction notes

Loading…