Dimethylformamide → HCID 13043093, compound

HRID 646593Notes

Reaction equation

HRID 646593 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10]C=1N)[C:6]([OH:8])=[O:7].[H-].[Na+].CI.[CH3:17][N:18]([CH:20]=O)[CH3:19]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:20]=1[N:18]([CH3:17])[CH3:19])[C:6]([OH:8])=[O:7]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2880572486-69-3

Product 1

HCID 13043093HCID 13043093, compound

Procedure

To a solution of 3-methoxy-4-aminobenzoic acid (1.5 g, 9 mmol) in DMF (10 mL) was added sodium hydride (60% in mineral oil, 1.5 g, 37.5 mmol) at 0° C. in portions. After stirring for 30 minutes, methyl iodide (6 g, 45 mmol) was added. The mixture was stirred overnight and quenched by addition of water. The aqueous mixture was extracted with dichloromethane (2×20 mL), dried over sodium sulfate and concentrated in vacuo. Purification by flash chromatography eluting with hexane/EtOAc (4:1) afforded 3-methoxy-4-dimethylaminobenzoic acid as an oil (1.8 g).

Workup

  1. stirringThe mixture was stirred overnight
  2. customquenched by addition of water
  3. extractionThe aqueous mixture was extracted with dichloromethane (2×20 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography
  7. washeluting with hexane/EtOAc (4:1)

Sources & evidence

ORD record
ord-4025e19a008241329bd5415789717ac9
Source dataset
uspto-grants-2010_04
Patent number
US07705151B2

Reaction notes

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