Isatoic Anhydride → (2-Aminophenyl)(pyrrolidin-1-yl)methanone

HRID 373115Notes

Reaction equation

HRID 373115 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6]C(=O)[O:4][C:2]2=O.[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1>CN(C)C1C=CN=CC=1.O1CCCC1>[NH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=1[C:2]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:4]

Participants

5

Reactant 2

HCID 8359Isatoic AnhydrideHCID 31268Pyrrolidine

Product 1

HCID 713136(2-Aminophenyl)(pyrrolidin-1-yl)methanone

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

17.5 g isatoic anhydride and 2.66 g 4-dimethylaminopyridine are combined in 500 ml tetrahydrofuran. 9.32 g of pyrrolidine is added and the mixture is heated at reflux overnight. The mixture is concentrated in vacuo, the residue taken into ethyl acetate and the organic solution washed with citric acid solution, water and brine and dried over magnesium sulfate. The solution is filtered, evaporated and the residue triturated in ether/hexane (1:5) to give N-(2-aminobenzoyl)pyrrolidine, m.p. 79°-81° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux overnight
  3. concentrationThe mixture is concentrated in vacuo
  4. washthe organic solution washed with citric acid solution, water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationThe solution is filtered
  7. customevaporated
  8. customthe residue triturated in ether/hexane (1:5)

Sources & evidence

ORD record
ord-8029186e417c4d9f90a53fd71150c370
Source dataset
uspto-grants-1992_11
Patent number
US05162336

Reaction notes

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