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

HRID 323452Notes

Reaction equation

HRID 323452 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 aqueous layer 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 aqueous layer 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-ceb4242dc9cb476e92066dd0b5a8b12c
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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