Water → HCID 54008458, compound

HRID 126933Notes

Reaction equation

HRID 126933 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:30])[CH:7]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]=1[N+:27]([O-:29])=[O:28])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:4].[CH3:31]I.O>CN(C)C=O>[CH2:11]([O:10][C:8](=[O:9])[C:7]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]=1[N+:27]([O-:29])=[O:28])([CH3:31])[C:6]([O:5][CH2:3][CH3:4])=[O:30])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15634748HCID 15634748, compound

Product 1

HCID 54008458HCID 54008458, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A slurry of 0.6 g (0.012 mole) of 50% sodium hydride/oil (washed, petroleum ether) in a 10 ml dimethylformamide was treated dropwise with a solution of 3.6 g (0.009 mole) of 2-(3-benzoyl-2-nitrophenyl)propanedioic acid diethyl ester in 20 ml of dimethylformamide. The mixtue was stirred for 5 min and the 4 ml (9.1 g, 0.065 mole) of methyliodide was added and the solution stirred at ambient temperature overnight. The solution was poured into 500 ml of cold water and let stand overnight. The aqueous layer was decanted and the gummy residue was dissolved in diethylether. The ether solution was washed with water and saturated sodium chloride solution, dried over sodium sulfate and concentrated to give 3.5 g (95%) of a gray solid, m.p. 102°-104° C. (recrystallized from 2-propanol).

Workup

  1. stirringthe solution stirred at ambient temperature overnight
  2. waitlet stand overnight
  3. customThe aqueous layer was decanted
  4. dissolutionthe gummy residue was dissolved in diethylether
  5. washThe ether solution was washed with water and saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customto give
  9. custom3.5 g (95%) of a gray solid, m.p. 102°-104° C. (recrystallized from 2-propanol)

Sources & evidence

ORD record
ord-6a7b5dff7fb6424c85fd157b69b195c4
Source dataset
uspto-grants-1981_03
Patent number
US04254146

Reaction notes

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