Methyl iodide → Methyl 5-methoxy-2-nitrobenzoate

HRID 1095006Notes

Reaction equation

HRID 1095006 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:12]([O-:14])=[O:13])=[C:7]([CH:11]=1)[C:8]([OH:10])=[O:9].[C:15](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O.C(OC(=O)C1C=C(OCCOC)C(OCCOC)=CC=1N)C>[CH3:15][O:9][C:8](=[O:10])[C:7]1[CH:11]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=1[N+:12]([O-:14])=[O:13]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 3392095-Methoxy-2-nitrobenzoic acid

Product 1

HCID 12719167Methyl 5-methoxy-2-nitrobenzoateYield 100.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 11347513Ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoateSolvent

Procedure

5-Methoxy-2-nitro-benzoic acid (2.5 g) was dissolved in N,N-dimethylformamide (compound A′) (40 ml). Potassium carbonate (4.5 g) and methyl iodide (2.5 ml) were added to the solution at room temperature, and the mixture was then stirred at that temperature for 30 min. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was then subjected to separatory extraction with ethyl acetate. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a hexane-acetone system to give 5-methoxy-2-nitrobenzoic acid methyl ester (2.7 g, yield 100%).

Workup

  1. customAfter the completion of the reaction
  2. distillationdistilled water
  3. additionwas added
  4. extractionat room temperature, and the mixture was then subjected to separatory extraction with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialwas dried over sodium sulfate
  7. concentrationwas then concentrated under the reduced pressure
  8. customThe residue was purified by column chromatography
  9. washeluted with a hexane-acetone system

Sources & evidence

ORD record
ord-66c74d10c9cf484288d2a53e3b2a5b85
Source dataset
uspto-grants-2012_03
Patent number
US08134015B2

Reaction notes

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