Pyridine → N-[4-Methoxy-3-(methoxycarbonyl)phenyl]ethanimidic acid

HRID 2230650Notes

Reaction equation

HRID 2230650 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].N1C=CC=CC=1.[C:20](OC(=O)C)(=[O:22])[CH3:21]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([NH:13][C:20](=[O:22])[CH3:21])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 89843Methyl 5-amino-o-anisate

Product 1

HCID 4153338N-[4-Methoxy-3-(methoxycarbonyl)phenyl]ethanimidic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Combine methyl 2-methoxy-5-aminobenzoate (2.0 g, 11 mmol), pyridine, 2.8 mL, 35 mmol), and acetic anhydride (3.2 mL, 34 mmol) in tetrahydrofuran (50 mL). After 20 hours, concentrate the reaction mixture in vacuo to remove most of the tetrahydrofuran, partition between ethyl acetate and water. Separate the layers and extract the aqueous layer twice with ethyl acetate. Combine the organic layers, extract with brine, dry over MgSO4, filter, and evaporate in vacuo to give a residue. Crystallize the residue from ethyl acetate/cyclohexane to give methyl 2-methoxy-5-acetamidobenzoate.

Workup

  1. concentrationconcentrate the reaction mixture in vacuo
  2. customto remove most of the tetrahydrofuran
  3. custompartition between ethyl acetate and water
  4. customSeparate the layers
  5. extractionextract the aqueous layer twice with ethyl acetate
  6. extractionextract with brine
  7. dry with materialdry over MgSO4
  8. filtrationfilter
  9. customevaporate in vacuo
  10. customto give a residue
  11. customCrystallize the residue from ethyl acetate/cyclohexane

Sources & evidence

ORD record
ord-b25e3e1868dd4df9b75c5a7aef3b8cae
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

Loading…