m-Toluidine → HCID 86688159, compound

HRID 2407347Notes

Reaction equation

HRID 2407347 reaction equation
F[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N+:12]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=1[NH:15][C:16]1[CH:17]=[C:18]([CH3:22])[CH:19]=[CH:20][CH:21]=1)[C:6]([O:8][CH3:9])=[O:7])([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 7934m-ToluidineHCID 11430Potassium CarbonateHCID 5219721Methyl 4-fluoro-3-nitrobenzoate

Product 1

HCID 86688159HCID 86688159, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The compound obtained in Step 1 (1.30 g, 6.53 mmol), m-toluidine (1.40 g, 13.1 mmol), and potassium carbonate (870 mg, 6.53 mmol) were dissolved in acetonitrile, and then stirred under reflux for 12 hours. The solvent was removed by concentration under reduced pressure, and then the precipitate generated by adding hexane thereto was filtered and washed with hexane, to obtain methyl 3-nitro-4-(m-tolylamino)benzoate as an orange solid (1.37 g, 73%).

Workup

  1. temperatureunder reflux for 12 hours
  2. customThe solvent was removed by concentration under reduced pressure
  3. additionby adding hexane
  4. filtrationthereto was filtered
  5. washwashed with hexane

Sources & evidence

ORD record
ord-3d0558337d64446294c911cdd56dbe56
Source dataset
uspto-grants-2014_08
Patent number
US08809541B2

Reaction notes

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