Reacción #1605772

ord-684e4b93eb264e9eb912c3a906b4b0a4

Ecuación de reacción

N
NH3
COc1cc(C)ccc1C(=O)O
2-methoxy-4-methylbenzoic acid
ClCCCl
EDC
On1nnc2ccccc21
HOBt
COc1cc(C)ccc1C(N)=O
2-methoxy-4-methylbenzamide
Rendimiento 83.0%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Lavadothen washed successively with HCl (1N)
  2. 2
    SecadoNaHCO3, water and brine, dried over MgSO4
  3. 3
    Filtraciónfiltered
  4. 4
    Otroevaporated
  5. 5
    OtroThe residue was recrystallized from ethyl acetate/hexane

Procedimiento

To a mixture of 2-methoxy-4-methylbenzoic acid (20 g, 120.4 mmol), EDC (23.1 g, 120.4 mmol) and HOBt (16.3 g, 120.4 mmol) in dichloromethane (1 L) was added NH3 (7N in MeOH, 52 mL, 3 eq) dropwise. The reaction mixture was stirred at room temperature overnight then washed successively with HCl (1N), saturated aq.NaHCO3, water and brine, dried over MgSO4, filtered and evaporated. The residue was recrystallized from ethyl acetate/hexane to give 16.5 gr of 2-methoxy-4-methylbenzamide (83% yield).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09072313B2uspto-grants-2015_07