Ethyl 2-aminobenzoate → HCID 15657978, compound

HRID 1655581Notes

Reaction equation

HRID 1655581 reaction equation
[C:1]([O:10][CH2:11][CH3:12])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].C(=O)([O-])[O-].[K+].[K+].[CH2:19](I)[CH2:20][CH2:21][CH3:22]>C(OCC)(=O)C>[CH2:19]([NH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([O:10][CH2:11][CH3:12])=[O:9])[CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 6877Ethyl 2-aminobenzoateHCID 10962Butyl iodideHCID 11430Potassium Carbonate

Product 1

HCID 15657978HCID 15657978, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ethyl anthranilate (4.96 g, 30 mmol), potassium carbonate (13.8 g, 100 mmol), and n-butyl iodide (25 mL) was stirred at ambient temperature for 48 hours and refluxed for 8 hours. The cooled reaction mixture was diluted with ethyl acetate and filtered. The filtrate was concentrated under reduced pressure and the residue obtained chromatographed eluting with ethyl acetate/hexane mixtures to afford the title comound as a light yellow liquid (2.2 g, 33%).

Workup

  1. temperaturerefluxed for 8 hours
  2. customThe cooled reaction mixture
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue obtained
  6. customchromatographed
  7. washeluting with ethyl acetate/hexane

Sources & evidence

ORD record
ord-de0eebd7dc75479195c12b672213ccf8
Source dataset
uspto-grants-1993_10
Patent number
US05250548

Reaction notes

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