Methyl Anthranilate → Methyl 2-anilinobenzoate

HRID 1977669Notes

Reaction equation

HRID 1977669 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].I[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu].C(OCC)(=O)C>[C:13]1([NH:1][C:2]2[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 8635Methyl AnthranilateHCID 11430Potassium CarbonateHCID 11575Iodobenzene

Product 1

HCID 607074Methyl 2-anilinobenzoateYield 90%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of methyl 2-aminobenzoate (7 g), iodobenzene (3.9 ml), potassium carbonate (6.4 g), and copper powder (0.46 g) was heated at 180° C. for 17 hours. The reaction solution was allowed to cool to room temperature, and ethyl acetate was added thereto. The resulting mixture was stirred and filtered with celite. The filtrate was washed with ethyl acetate and concentrated under reduced pressure. The thus-obtained residue was purified by silica gel column chromatography (developing solvent, ethyl acetate: hexane=1:30) to obtain methyl 2-phenylaminobenzoate (7.13 g; yield, 90%) as a pale yellow solid.

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered with celite
  3. washThe filtrate was washed with ethyl acetate
  4. concentrationconcentrated under reduced pressure
  5. customThe thus-obtained residue was purified by silica gel column chromatography (developing solvent, ethyl acetate: hexane=1:30)

Sources & evidence

ORD record
ord-363e4577999a4633987a88e5226c285a
Source dataset
uspto-grants-2001_05
Patent number
US06235730B1

Reaction notes

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