Potassium Iodide → Methyl 4-[formyl-(2-oxopropyl)amino]-3-methoxybenzoate

HRID 599533Notes

Reaction equation

HRID 599533 reaction equation
Cl[CH2:2][C:3](=[O:5])[CH3:4].[CH:6]([NH:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1[O:19][CH3:20])=[O:7].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH:6]([N:8]([CH2:2][C:3](=[O:5])[CH3:4])[C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1[O:19][CH3:20])=[O:7]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 6571Chloroacetone2×HCID 10796Cesium carbonate2×HCID 23085082Methyl 4-formamido-3-methoxybenzoate

Product 1

HCID 86602464Methyl 4-[formyl-(2-oxopropyl)amino]-3-methoxybenzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Chloroacetone (84.5 mL) was added dropwise to a mixture of methyl 4-formylamino-3-methoxybenzoate (111 g), cesium carbonate (346 g), and potassium iodide (8.78 g) in DMF (497 mL) at room temperature, and the reaction solution was stirred for three hours. Cesium carbonate (173 g) and chloroacetone (42.0 mL) were added to the reaction solution, which was then stirred at room temperature for two hours. Ice water and ethyl acetate were added to the reaction solution, and the organic layer was separated. Ethyl acetate was added to the aqueous layer, and the organic layer was separated. The organic layers were combined and washed with water and brine in this order. The resulting organic layers were dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was diluted with toluene, and the solution was concentrated under reduced pressure. tert-Butyl methyl ether and heptane were added to the resulting residue, and the precipitated solid was collected by filtration and washed with a solution of 50% tert-butyl methyl ether in heptane. The resulting solid was air-dried overnight to obtain 118 g of the title compound.

Workup

  1. stirringwas then stirred at room temperature for two hours
  2. customthe organic layer was separated
  3. additionEthyl acetate was added to the aqueous layer
  4. customthe organic layer was separated
  5. washwashed with water and brine in this order
  6. dry with materialThe resulting organic layers were dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. additionThe residue was diluted with toluene
  9. concentrationthe solution was concentrated under reduced pressure
  10. additiontert-Butyl methyl ether and heptane were added to the resulting residue
  11. filtrationthe precipitated solid was collected by filtration
  12. washwashed with a solution of 50% tert-butyl methyl ether in heptane
  13. customThe resulting solid was air-dried overnight

Sources & evidence

ORD record
ord-16f6497428e040b6ab3a3441e8ece3c3
Source dataset
uspto-grants-2011_03
Patent number
US07897632B2

Reaction notes

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