Pyrrolidine → 3-Amino-4-(1-pyrrolidinylmethyl)benzoic acid

HRID 248709

Reaction equation

HRID 248709 reaction equation
Br[CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[N+:12]([O-])=O.[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1>ClCCl>[NH2:12][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:3]=1[CH2:2][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 1323864-Bromomethyl-3-nitrobenzoic acid

Product 1

HCID 156703753-Amino-4-(1-pyrrolidinylmethyl)benzoic acidYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Bromomethyl-3-nitrobenzoic acid (10 g) is dissolved in dichloromethane (100 ml) and thereto is added dropwise pyrrolidine (8 g) with stirring under ice cooling, and the mixture is stirred at room temperature for 30 minutes. Dichloromethane is distilled off under reduced pressure, and the residue is dissolved in conc. hydrochloric acid (40 ml) and thereto is added water (10 ml) with stirring under ice cooling and further is added tin (5.4 g), and the mixture is stirred under ice cooling for 1.5 hour. The reaction mixture is neutralized with 10N aqueous sodium hydroxide solution, and the catalyst is filtered off and the filtrate is concentrated. The residue is dissolved in water and purified by a medium pressure column chromatography with CHP-20P (eluant, water-acetonitrile). The fractions containing the desired compound are collected, and concentrated into dryness under reduced pressure to give 3-amino-4-(1-pyrrolidinylmethyl)benzoic acid (7.2 g).

Workup

  1. stirringthe mixture is stirred at room temperature for 30 minutes
  2. distillationDichloromethane is distilled off under reduced pressure
  3. dissolutionthe residue is dissolved in conc. hydrochloric acid (40 ml)
  4. additionis added water (10 ml)
  5. stirringwith stirring under ice cooling
  6. additionfurther is added tin (5.4 g)
  7. stirringthe mixture is stirred under ice cooling for 1.5 hour
  8. filtrationthe catalyst is filtered off
  9. concentrationthe filtrate is concentrated
  10. dissolutionThe residue is dissolved in water
  11. custompurified by a medium pressure column chromatography with CHP-20P (eluant, water-acetonitrile)
  12. additionThe fractions containing the desired compound
  13. customare collected
  14. concentrationconcentrated into dryness under reduced pressure

Sources & evidence

ORD record
ord-e4f1c9c80e1c41b1a0032d693db6c0e1
Source dataset
uspto-grants-1993_05
Patent number
US05210266

Linked notes

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