Sodium Carbonate → 4-(2-Oxopyrrolidin-1-yl)benzoic acid

HRID 1955136Notes

Reaction equation

HRID 1955136 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O-:8])=[O:7])=[CH:4][CH:3]=1.[Na+].Cl[CH2:13][CH2:14][CH2:15][C:16](Cl)=[O:17].C([O-])([O-])=O.[Na+].[Na+]>C1C=CC=CC=1>[O:17]=[C:16]1[CH2:15][CH2:14][CH2:13][N:1]1[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 783704-Chlorobutyryl chlorideHCID 517441Sodium 4-aminobenzoate

Product 1

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

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
60 °C

Procedure

Sodium 4-aminobenzoate (42.5 g,0.267 mol) was suspended in 250 ml benzene. To this solution, upon vigorous stirring, 4-chlorobutyryl chloride (29 ml, 0.248 mol) was added slowly. The temperature of the reaction mixture was heated to 60° C. It is at 60° C. that the reaction was continued for another 20 hours. Na2CO3 solution (20%, 600 ml) was then added and the benzene layer was separated. The aqueous layer was acidified and the white precipitate was filtrated and recrystallized from methanol to form colorless crystal of 4-(2-oxo-pyrrolidin-1-yl)-benzoic acid. Mass Spectra: m/e (relative intensity) 205(M+, 44.23).

Workup

  1. customis at 60° C. that the reaction
  2. customthe benzene layer was separated
  3. filtrationthe white precipitate was filtrated
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-e0662b7a0cb14e4c8b9a8a552bb10d5f
Source dataset
uspto-grants-2000_09
Patent number
US06124365

Reaction notes

Loading…