Methyl iodide → 3-(Methyl(phenyl)amino)benzoic acid

HRID 1777575Notes

Reaction equation

HRID 1777575 reaction equation
[H-].[Na+].[C:3]1([NH:9][C:10]2[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=2)[C:13]([O:15]CC)=[O:14])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:21]I>C1COCC1.O>[CH3:21][N:9]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=1)[C:13]([OH:15])=[O:14]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 69991060Ethyl 3-(phenylamino)benzoate

Product 1

HCID 211061273-(Methyl(phenyl)amino)benzoic acidYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

NaH 60% in mineral oil (0.050 g; 1.23 mmol) was added to a solution of ethyl 3-(phenylamino)benzoate (0.198 g; 0.820 mmol) in THF (3 mL). After stirring the resulting solution for 10 minutes, methyl iodide (0.102 mL; 1.1.64 mmol) was added and the resulting mixture was stirred overnight at room temperature. The mixture was diluted in water and extracted with ethyl acetate. The organic layer was washed with brine and dried to yield 0.056 g (30%) of the title compound as a colourless solid which was used without further purifications.

Workup

  1. stirringthe resulting mixture was stirred overnight at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. customdried

Sources & evidence

ORD record
ord-44ab9f0c1fc84e0db13b1555285471fc
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

Loading…