Sodium hydride → Ethyl 3-bromo-5-(2-oxo-1-pyrrolidinyl)benzoate

HRID 269561Notes

Reaction equation

HRID 269561 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([CH:12]=[C:13]([NH:15][C:16](=[O:21])[CH2:17][CH2:18][CH2:19]Cl)[CH:14]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8]>C1COCC1>[Br:3][C:4]1[CH:5]=[C:6]([CH:12]=[C:13]([N:15]2[CH2:19][CH2:18][CH2:17][C:16]2=[O:21])[CH:14]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 69312186Ethyl 3-bromo-5-[(4-chlorobutanoyl)amino]benzoate

Product 1

HCID 69310922Ethyl 3-bromo-5-(2-oxo-1-pyrrolidinyl)benzoateYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride, 60% suspension in oil (186 mg, 4.65 mmol) was added portionwise over 2 mins to a solution of ethyl 3-bromo-5-[(4-chlorobutanoyl)amino]benzoate (1.35 g, 3.87 mmol) in dry THF (50 ml) under nitrogen. The reaction mixture was stirred at room temperature for 2 hours. The reaction was quenched by the careful addition of water (25 ml). Diethyl ether (50 ml) was added. The organic phase was washed with water, dried and evaporated to give the title compound as a yellow solid (990 mg, 82%).

Workup

  1. customThe reaction was quenched by the careful addition of water (25 ml)
  2. additionDiethyl ether (50 ml) was added
  3. washThe organic phase was washed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-9e48a4e796894b0e8085b0dec450e126
Source dataset
uspto-grants-2008_11
Patent number
US07446222B2

Reaction notes

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