Reacción #2439961

ord-cb9e5286896c4fb5b91ec277f5e865ba

Ecuación de reacción

O=C1Cc2cc(Cc3ccc([N+](=O)[O-])cc3)ccc2N1
5-(4-Nitro-benzyl)-1,3-dihydro-indol-2-one
Nc1ccc(Cc2ccc3c(c2)CC(=O)N3)cc1
5-(4-Amino-benzyl)-1,3-dihydro-indol-2-one
Rendimiento 58.0%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe flask was evacuated
  2. 2
    workup.ADDITIONthen charged with H2(g) (55 psi)
  3. 3
    Otroto degas the reaction mixture)
  4. 4
    workup.ADDITIONThe reaction vessel charged with H2(g) (55 psi)
  5. 5
    Filtraciónwere filtered through celite
  6. 6
    ConcentraciónThe organic solution was then concentrated in vacuo

Procedimiento

5-(4-Nitro-benzyl)-1,3-dihydro-indol-2-one (0.524 g, 1.94 mmols) was suspended in 35 ml of MeOH. 5% Pd/C (50 mg) was added to the flask which then was placed on a PARR apparatus. The flask was evacuated then charged with H2(g) (55 psi). This evacuation/H2(g) fill procedure was repeated 3 times (to degas the reaction mixture). The reaction vessel charged with H2(g) (55 psi) was shaken on the PARR apparatus for 2.5 hours after which the contents were filtered through celite. The organic solution was then concentrated in vacuo affording 5-(4-Amino-benzyl)-1,3-dihydro-indol-2-one at 58% yield (0.267 g, 1.12 mmol).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07749530B2uspto-grants-2010_07