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

HRID 1446443Notes

Reaction equation

HRID 1446443 reaction equation
Cl[CH2:2][C:3](=[O:5])[CH3:4].[CH3:6][O:7][C:8](=[O:20])[C:9]1[CH:14]=[CH:13][C:12]([NH:15][CH:16]=[O:17])=[C:11]([O:18][CH3:19])[CH:10]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>C(OCC)(=O)C.O.CN(C=O)C>[CH3:6][O:7][C:8](=[O:20])[C:9]1[CH:14]=[CH:13][C:12]([N:15]([CH:16]=[O:17])[CH2:2][C:3](=[O:5])[CH3:4])=[C:11]([O:18][CH3:19])[CH:10]=1

Participants

8

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 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Chloroacetone (84.5 mL) was added dropwise to the DMF (497 mL) mixture of 4-formylamino-3-methoxybenzoic acid methyl ester (111 g), cesium carbonate (346 g), and potassium iodide (8.78 g) at room temperature, and the reaction mixture was agitated for 3 hours. Cesium carbonate (173 g) and chloroacetone (42.0 mL) were added to the reaction mixture, and the reaction mixture was agitated at room temperature for 2 hours. Iced water and ethyl acetate were added to the reaction mixture, and the organic layer was partitioned. Ethyl acetate was added to the aqueous layer and the organic layer was partitioned. The organic layers were combined, washed with water and a saturated saline solution in this order, and the obtained organic layer was 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-butylmethyl ether and heptane were added to the resulted residue and the deposited solids were separated by filtering and washed with a 50% heptane solution of tert-butylmethyl ether. 118 g of the title compound was obtained by air-drying the obtained solids overnight.

Workup

  1. stirringthe reaction mixture was agitated at room temperature for 2 hours
  2. customthe organic layer was partitioned
  3. additionEthyl acetate was added to the aqueous layer
  4. customthe organic layer was partitioned
  5. washwashed with water
  6. dry with materiala saturated saline solution in this order, and the obtained organic layer was 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-butylmethyl ether and heptane were added to the resulted residue
  11. customthe deposited solids were separated
  12. filtrationby filtering
  13. washwashed with a 50% heptane solution of tert-butylmethyl ether

Sources & evidence

ORD record
ord-3164b0df79c947279236bef1371c4755
Source dataset
uspto-grants-2010_02
Patent number
US07667041B2

Reaction notes

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