Water → methyl 5-(4-bromo-2-formyl-N-propylanilino)pentanoate

HRID 2222818Notes

Reaction equation

HRID 2222818 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]([N:6]([CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH2:7][CH2:8][CH3:9])=[C:4]([CH:19]=[O:20])[CH:3]=1.[C:21](=O)([O-])[O-].[K+].[K+].IC.O>CN(C=O)C>[Br:1][C:2]1[CH:18]=[CH:17][C:5]([N:6]([CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:21])=[O:15])[CH2:7][CH2:8][CH3:9])=[C:4]([CH:19]=[O:20])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 865955795-(4-bromo-2-formyl-N-propylanilino)pentanoic acid

Product 1

HCID 86595580methyl 5-(4-bromo-2-formyl-N-propylanilino)pentanoateYield 94.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 5-(4-bromo-2-formyl-N-propylanilino)pentanoic acid (8.00 g) and potassium carbonate (3.88 g) in DMF (25 ml) was added dropwise a solution of iodomethane (4.66 g) in DMF (5 ml) under a nitrogen atmosphere. The mixture was stirred overnight under a nitrogen atmosphere. Then, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline and dried over magnesium sulfate. The solvent was distilled off under reduced pressure to obtain brown oil of methyl 5-(4-bromo-2-formyl-N-propylanilino)pentanoate (7.89 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated saline
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-cef76461ae95446e9e5608b60baccd51
Source dataset
uspto-grants-2008_05
Patent number
US07371772B2

Reaction notes

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