Aniline → 1-Cyclopentene-1-carboxylic acid, 2-(phenylamino)-, ethyl ester

HRID 366386Notes

Reaction equation

HRID 366386 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][CH2:9][O:10][C:11]([CH:13]1[C:17](=O)[CH2:16][CH2:15][CH2:14]1)=[O:12].[Cl-].[Ca+2].[Cl-]>C1COCC1>[NH:1]([C:14]1[CH2:15][CH2:16][CH2:17][C:13]=1[C:11]([O:10][CH2:9][CH3:8])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 69136Ethyl 2-oxocyclopentanecarboxylateHCID 5284359Calcium Chloride

Product 1

HCID 113792411-Cyclopentene-1-carboxylic acid, 2-(phenylamino)-, ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of aniline (6.0 g, 64.5 mmol), ethyl cyclopentanone-2-carboxylate (Aldrich Chemicals) (10.0 g, 64.1 mmol) and calcium chloride (7.6 g, 68.5 mmol) in THF (100 ml) was heated under reflux for 24 hours. After being allowed to cool, the suspension was filtered and the solvent was removed from the filtrate under reduced pressure. Kugelrohr distillation of the residue (125° C., 0.02 mmHg) gave the title product as a pale yellow liquid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. temperatureto cool
  4. filtrationthe suspension was filtered
  5. customthe solvent was removed from the filtrate under reduced pressure
  6. distillationKugelrohr distillation of the residue (125° C., 0.02 mmHg)

Sources & evidence

ORD record
ord-3ad618fb96be4a528261b02fd52d732b
Source dataset
uspto-grants-2000_10
Patent number
US06130228

Reaction notes

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