Citric Acid → 3-nitro-4-pyrrolidin-1-ylbenzoic acid

HRID 1646281Notes

Reaction equation

HRID 1646281 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[CH2:14]([N:16](CC)[CH2:17][CH3:18])[CH3:15].N1CCCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1(C)C(C)=CC=CC=1>[N+:11]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:2]=1[N:16]1[CH2:17][CH2:18][CH2:15][CH2:14]1)[C:6]([OH:8])=[O:7])([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 73204-Chloro-3-nitrobenzoic acidHCID 8471TriethylamineHCID 31268Pyrrolidine

Product 1

HCID 36719303-nitro-4-pyrrolidin-1-ylbenzoic acidYield 96%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

4-Chloro-3-nitrobenzoic acid (5.0 g) is suspended in xylene (50 ml), and thereto are added triethylamine (2.5 g) and pyrrolidine (2.0 g), and the mixture is refluxed for 2 hours. To the reaction mixture is added 10% aqueous citric acid solution, and the precipitated crystals are separated by filtration, washed with water and dried to give 3-nitro-4-(1-pyrrolidinyl)benzoic acid (5.6 g).

Workup

  1. temperaturethe mixture is refluxed for 2 hours
  2. customthe precipitated crystals are separated by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-535f466708904b3b804753fcc71962c1
Source dataset
uspto-grants-1993_01
Patent number
US05179125

Reaction notes

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