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

HRID 2116762Notes

Reaction equation

HRID 2116762 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+].Cl[CH2:14][CH2:15][CH2:16][C:17](Cl)=[O:18].Cl>O.C1(C)C=CC=CC=1>[N:1]1([C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=2)[CH2:14][CH2:15][CH2:16][C:17]1=[O:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9784-Aminobenzoic AcidHCID 14798Sodium Hydroxide3×HCID 783704-Chlorobutyryl chloride

Product 1

HCID 7731304-(2-Oxopyrrolidin-1-yl)benzoic acidYield 96.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
17.5 °C

Procedure

4-Aminobenzoic acid (100 g, 0.73 mol) is suspended in water (400 mL) and toluene (200 mL), and thereto is added dropwise 30% aqueous sodium hydroxide solution (97 g, 0.73 mol) under ice-cooling. After confirming that pH is basic enough, 4-chlorobutyric chloride (103 g, 0.73 mol) and 30% aqueous sodium hydroxide solution (290 g, 2.2 mol) are added dropwise simultaneously while maintaining the pH range of 9-12 and temperature range of 15-20° C. over 1 hour. After stirring at room temperature for 1 hour, sodium hydroxide (88 g, 2.2 mol) is added to the mixture under ice-cooling. To the reaction solution is added conc. hydrochloric acid (370 g) at 30° C. or below and precipitated crystals are collected by filtration. The resulting crystals are washed with water and air-dried at 40° C. to give 4-(2-pyrrolidon-1-yl)benzoic acid (144 g, yield: 96.0%, purity: 98.3%). The purity was determined by HPLC analysis.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. customprecipitated crystals
  4. filtrationare collected by filtration
  5. washThe resulting crystals are washed with water
  6. customair-dried at 40° C.

Sources & evidence

ORD record
ord-5ebba97757ac42289b6a02023303760f
Source dataset
uspto-grants-2008_10
Patent number
US07439368B2

Reaction notes

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