Methyl iodide → 4-(Methyl(phenyl)amino)benzoic acid

HRID 1777574Notes

Reaction equation

HRID 1777574 reaction equation
[H-].[Na+].[C:3]1([NH:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=[O:15])=[CH:12][CH:11]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:20]I>C1COCC1.O>[CH3:20][N:9]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[C:10]1[CH:19]=[CH:18][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 614877Methyl 4-anilinobenzoate

Product 1

HCID 232051694-(Methyl(phenyl)amino)benzoic acidYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

NaH 60% dispersed in mineral oil (0.030 g; 0.745 mmol) was added to a solution of methyl 4-(phenylamino)benzoate (0.113 g; 0.497 mmol) in THF (3 mL). After stirring the resulting solution for 10 minutes, methyl iodide (0.062 mL; 0.994 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 0.045 g (40%) of the title compound as a white solid.

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-9bf10752906741ec9a68190ae6791deb
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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