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

HRID 2076266Notes

Reaction equation

HRID 2076266 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+]>C(OCC)(=O)C.CN(C=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 DMF (497 mL) mixture of methyl 4-formylamino-3-methoxybenzoate (111 g), cesium carbonate (346 g), and potassium iodide (8.78 g) at room temperature, and the reaction liquid was stirred for 3 hours. Cesium carbonate (173 g) and chloroacetone (42.0 mL) were further added to the reaction liquid, which was then stirred at room temperature for 2 hours. Ice water and ethyl acetate were added to the reaction liquid to separate an organic layer. Ethyl acetate was added to the aqueous layer to separate an organic layer. The organic layers were combined, which was then washed with water and saturated saline in that order, followed by drying the resultant organic layer with anhydrous magnesium sulfate before concentrating the organic layer under reduced pressure. The residue was diluted with toluene, followed by concentrating the solution under reduced pressure. To the resultant residue were added tertiary-butyl methyl ether and heptane, and the precipitated solid was collected by filtration and washed with a heptane solution of 50% tertiary-butyl methyl ether. The resultant solid was air-dried overnight to provide 118 g of the title compound.

Workup

  1. customthe reaction liquid
  2. stirringwas then stirred at room temperature for 2 hours
  3. customto separate an organic layer
  4. additionEthyl acetate was added to the aqueous layer
  5. customto separate an organic layer
  6. washwhich was then washed with water and saturated saline in that order
  7. dry with materialby drying the resultant organic layer with anhydrous magnesium sulfate
  8. concentrationbefore concentrating the organic layer under reduced pressure
  9. additionThe residue was diluted with toluene
  10. concentrationby concentrating the solution under reduced pressure
  11. additionTo the resultant residue were added tertiary-butyl methyl ether and heptane
  12. filtrationthe precipitated solid was collected by filtration
  13. washwashed with a heptane solution of 50% tertiary-butyl methyl ether
  14. customThe resultant solid was air-dried overnight

Sources & evidence

ORD record
ord-3be13e1eecdb4f9d98e3054e1d3745ae
Source dataset
uspto-grants-2011_04
Patent number
US07923563B2

Reaction notes

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