Sodium Formate → 4-formyl-N-(methoxyiminomethyl)-2-methyl benzoic acid amide

HRID 552664Notes

Reaction equation

Br[C:2]1[CH:14]=[CH:13][C:5]([C:6]([NH:8][CH:9]=[N:10][O:11][CH3:12])=[O:7])=[C:4]([CH3:15])[CH:3]=1.[CH:16]([O-])=[O:17].[Na+]>CN(C)C=O.O>[CH:16]([C:2]1[CH:14]=[CH:13][C:5]([C:6]([NH:8][CH:9]=[N:10][O:11][CH3:12])=[O:7])=[C:4]([CH3:15])[CH:3]=1)=[O:17]

Participants

Conditions

Temperature: 120 °C

Procedure

In a solution of 0.20 g of 4-bromo-N-(methoxyiminomethyl)-2-methyl benzoic acid amide in 5 ml of N,N-dimethylformamide, 0.065 g of sodium formate and 0.026 g of dichlorobis(triphenylphosphine) palladium (II) were added, and stirred under carbon monoxide atmosphere at 120° C. for 1.5 hour. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, and poured in 30 mL of water, and extracted with ethyl acetate (20 mL×2). The combined organic phases were washed with water, and dehydrated with and dried over saturated sodium chloride aqueous solution and then anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that were eluated with ethyl acetate-hexane (gradient of 1:3 to 1:1) to obtain 0.071 g of the aimed product as colorless oily substance.

Workup

customAfter the completion of the reaction
waitthe reaction mixture was left
temperaturecooled to room temperature
extractionextracted with ethyl acetate (20 mL×2)
washThe combined organic phases were washed with water
dry with materialdried over saturated sodium chloride aqueous solution
distillationanhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure
customThe residue was purified with silica gel column chromatography that

Sources & evidence

ORD record: ord-553d5fd055f04ccfb8a7b175b8d3f2b7
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951828B1

Reaction notes

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