Sodium Formate → HCID 86631561, compound

HRID 551327Notes

Reaction equation

HRID 551327 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][C:3]=1[CH2:9][NH:10][C:11]([CH:13]1[CH2:15][CH2:14]1)=[O:12].[CH:16]([O-])=[O:17].[Na+]>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([CH:16]=[O:17])[CH:5]=[CH:4][C:3]=1[CH2:9][NH:10][C:11]([CH:13]1[CH2:15][CH2:14]1)=[O:12]

Participants

5

Reactant 2

HCID 2723810Sodium FormateHCID 67189037HCID 67189037, compound

Product 1

HCID 86631561HCID 86631561, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

In a solution of 2.20 g of N-[(2-chloro-4-iodophenyl)methyl]cyclopropanecarboxamide and 0.57 g of sodium formate in 20 mL of N,N-dimethylformamide in an autoclave, 0.26 g of dichlorobis(triphenylphosphine) palladium (II) was added, and stirred under carbon monoxide atmosphere of 1.5 MPa at 90° C. for 1 hour. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, and diluted with 60 mL of ethyl acetate and washed with water (30 mL×2). The organic phase was dehydrated with and dried over saturated sodium chloride aqueous solution and anhydrous magnesium sulfate in that order, the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluted with ethyl acetate to obtain 1.20 g of the aimed product as white crystal.

Workup

  1. customAfter the completion of the reaction
  2. waitthe reaction mixture was left
  3. temperaturecooled to room temperature
  4. washwashed with water (30 mL×2)
  5. dry with materialdried over saturated sodium chloride aqueous solution and anhydrous magnesium sulfate in that order
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified with silica gel column chromatography that
  8. washwas eluted with ethyl acetate

Sources & evidence

ORD record
ord-7e20e019e95041f38a09c8575acb4f2b
Source dataset
uspto-grants-2011_05
Patent number
US07947715B2

Reaction notes

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