Reacción #1772006

ord-ffb4aacb7fa541ef834426a7624ca2f7

Ecuación de reacción

COc1ccc(N)cc1
p-Anisidine
c1ccncc1
pyridine
O=C(Cl)c1ccc([N+](=O)[O-])cc1
4-nitrobenzoyl chloride
O
water
COc1ccc(C(=O)Nc2ccc([N+](=O)[O-])cc2)cc1
4-Methoxy-4′-nitrobenzanilide

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrothe precipitate was collected with filtrate under vacuum pressure
  2. 2
    Lavadowashed with 5% sodium bicarbonate (2×10 ml)
  3. 3
    OtroThe product was used in the next step without further purification

Procedimiento

p-Anisidine (1.0 g, 8.1 mmol) was dissolved in anhydrous pyridine (15 ml), 4-nitrobenzoyl chloride (1.5 g, 8.1 mmol) was added. The reaction mixture was allowed to stand at room temperature for 16 hrs. The reaction mixture was poured into water and the precipitate was collected with filtrate under vacuum pressure and washed with 5% sodium bicarbonate (2×10 ml). The product was used in the next step without further purification. 1HNMR (300 MHz, DMSO-d6) δ: 10.46 (s, 1H, NH), 8.37 (d, J=5.5 Hz, 2H, H-3′,5′), 8.17 (d, J=6.3 Hz, 2H, H-2′,6′), 7.48 (d, J=6.6 Hz, 2H), 6.97 (d, J=6.5 Hz, 2H), 3.75 (s, 3H, MeO).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08147798B2uspto-grants-2012_04