Methyl 2-chloro-5-nitrobenzoate → HCID 53980342, compound

HRID 1761931Notes

Reaction equation

HRID 1761931 reaction equation
[C:1](=[N:9][OH:10])([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH3:2].[H-].[Na+].Cl[C:14]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17]>CN(C)C=O>[CH3:19][O:18][C:16]([C:15]1[CH:20]=[C:21]([N+:24]([O-:26])=[O:25])[CH:22]=[CH:23][C:14]=1[O:10][N:9]=[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH3:2])=[O:17]

Participants

5

Reactant 3

HCID 22754Methyl 2-chloro-5-nitrobenzoateHCID 24758Sodium hydrideHCID 69185Acetophenonoxime

Product 1

HCID 53980342HCID 53980342, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 17.25 g of acetophenone oxime in 100 ml of dimethylformamide is added dropwise to a suspension of 5.92 g of 62.5% sodium hydride in 400 ml of dimethylformamide under ice-cooling. The mixture is stirred at the same temperature for 1.5 hours. A solution of 25.04 g of methyl 2-chloro-5-nitrobenzoate in 150 ml of dimethylformamide is added to the mixture, the mixture is stirred for 1 hour. The reaction mixture is poured into ice-water and the aqueous mixture is extracted with ethyl acetate. The extract is washed with an aqueous saturated sodium chloride solution, dried and evaporated to remove solvent. The residue is recrystallized from isopropanol to give 26.7 g of acetophenone O-(2-methoxycarbonyl-4-nitrophenyl)oxime as yellow needles.

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred for 1 hour
  3. extractionthe aqueous mixture is extracted with ethyl acetate
  4. washThe extract is washed with an aqueous saturated sodium chloride solution
  5. customdried
  6. customevaporated
  7. customto remove solvent
  8. customThe residue is recrystallized from isopropanol

Sources & evidence

ORD record
ord-24e71003659b408291a138771af8b650
Source dataset
uspto-grants-1989_05
Patent number
US04829067

Reaction notes

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