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

HRID 402259Notes

Reaction equation

HRID 402259 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-ec383dc3e23c4f2e98c1485108d7a256
Source dataset
uspto-grants-2014_06
Patent number
US08741943B2

Reaction notes

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