Sodium hydride → HCID 69358200, compound

HRID 852637Notes

Reaction equation

HRID 852637 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH3:12])[CH:7]=[C:6]([NH:13][C:14](=[O:19])[CH2:15][CH2:16][CH2:17]Cl)[CH:5]=1.[H-].[Na+]>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:5]=[C:6]([N:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:19])[CH:7]=[C:8]([O:10][CH2:11][CH3:12])[CH:9]=1

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 69356535HCID 69356535, compound

Product 1

HCID 69358200HCID 69358200, compoundYield 66.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(4-Chloro-butanoylamino)-5-ethoxy-benzoic acid methyl ester (D51) (7 g, 20 mmol, 1 equiv) in THF (50 ml) was treated portionwise with NaH (60% in mineral oil, 0.88 g, 22 mmol, 1.1 equiv) over 15 min at room temperature. The resulting mixture was stirred for 30 min and then diluted with AcOEt (300 ml). The resulting solution was washed with 2N aqueous HCl solution (200 ml), dried over MgSO4 and concentrated in vacuo. Recrystallisation of the residue from Et2O/hexane gave 3-ethoxy-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester (B11) (3.5 g, 66%) as white solid.

Workup

  1. washThe resulting solution was washed with 2N aqueous HCl solution (200 ml)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customRecrystallisation of the residue from Et2O/hexane

Sources & evidence

ORD record
ord-0ea6754d525041eb907d3c604d5027bb
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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