Reacción #2006409

ord-14399f5a2c154714b855a8c46104f99a

Ecuación de reacción

O=C([O-])O.[Na+]
NaHCO3
Nc1cccc(CC(=O)O)c1
3-aminophenylacetic acid
Cl
HCl
COC(=O)Cc1cccc(N)c1
1
Rendimiento 79.0%
COC(=O)Cc1cccc(N)c1
Methyl-3-aminophenylacetate
Rendimiento 79.0%

Reactivos

Ninguno

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe solvent was removed under reduced pressure
  2. 2
    Extracciónthe aqueous phase was extracted several times with CH2Cl2
  3. 3
    SecadoThe combined organic extracts were dried over (MgSO4)
  4. 4
    Otroevaporated
  5. 5
    OtroThe crude mixture was purified by flash chromatography

Procedimiento

To a solution of 3-aminophenylacetic acid (3 g, 19.85 mmol) in methanol (50 mL) at room temperature was added HCl conc. (37%, 7.5 mL). The mixture was stirred 6 h at room temperature then treated with a saturated aqueous solution of NaHCO3. The solvent was removed under reduced pressure then the aqueous phase was extracted several times with CH2Cl2. The combined organic extracts were dried over (MgSO4) and evaporated. The crude mixture was purified by flash chromatography using hexane/AcOEt (1:1) yielding 1 as a yellow oil (3.06 g, 79%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: USRE043343E1uspto-grants-2012_05