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

HRID 71136Notes

Reaction equation

HRID 71136 reaction equation
[CH:1]([NH:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[O:14][CH3:15])=[O:2].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:23][C:24](=[O:26])[CH3:25].C(OCC)(=O)C>CN(C=O)C.[I-].[K+]>[CH:1]([N:3]([CH2:23][C:24](=[O:26])[CH3:25])[C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[O:14][CH3:15])=[O:2]

Participants

7

Reactant 4

HCID 6571Chloroacetone2×HCID 8857Ethyl AcetateHCID 10796Cesium carbonate2×HCID 23085082Methyl 4-formamido-3-methoxybenzoate

Product 1

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

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a mixture of methyl 4-(formylamino)-3-methoxybenzoate (25.8 g), cesium carbonate (80.4 g) and potassium iodide (2.04 g) in DMF (115 mL) was added dropwise chloroacetone (19.6 mL) at room temperature, and the mixture was stirred at room temperature for 3 hr. Cesium carbonate (40.2 g) and chloroacetone (9.8 mL) were added to the reaction mixture, and the mixture was stirred at room temperature for 2 hr. Ice water and ethyl acetate were added to the reaction mixture, and the organic layer was separated. To the aqueous layer was added ethyl acetate, and the organic layer was separated. The organic layers were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (32.6 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hr
  2. customthe organic layer was separated
  3. additionTo the aqueous layer was added ethyl acetate
  4. customthe organic layer was separated
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e3d04af8db2a49d1a86c605a59b8f46e
Source dataset
uspto-grants-2014_09
Patent number
US08822699B2

Reaction notes

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