Reacción #217907

ord-ac9f9a605430414ea11139c1849030e1

Ecuación de reacción

Cc1cc(C=O)ccc1O
4-hydroxy-3-methylbenzaldehyde
O=C([O-])[O-].[K+].[K+]
K2CO3
NC(=O)c1ccc(Cl)nc1
6-chloronicotinamide
O
H2O
[NH4+].[OH-]
NH4OH
Rendimiento 0.7%
Cc1cc(C=O)ccc1Oc1ccc(C(N)=O)cn1
title compound
Cc1cc(C=O)ccc1Oc1ccc(C(N)=O)cn1
6-(4-Formyl-2-methyl-phenoxy)-nicotinamide

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otroirradiated for 5 min
  2. 2
    OtroUpon completion of the reaction
  3. 3
    Temperaturathe mixture was cooled
  4. 4
    Extracciónextracted with ethyl acetate
  5. 5
    Lavadothe combined organic layers were washed twice with water and brine
  6. 6
    OtroAfter drying the extracts
  7. 7
    Otroover magnesium sulfate and evaporation under vacuum the crude product
  8. 8
    Otrowas purified by silica gel chromatography

Procedimiento

A solution of 4-hydroxy-3-methylbenzaldehyde (1.0 equiv) in DMF (0.2 M solution) was treated with K2CO3 (1.5 equiv) and 6-chloronicotinamide (1.0 equiv). The reaction mixture was placed inside the microwave oven and then irradiated for 5 min. Upon completion of the reaction, the mixture was cooled, poured into H2O and extracted with ethyl acetate, and the combined organic layers were washed twice with water and brine. After drying the extracts over magnesium sulfate and evaporation under vacuum the crude product was purified by silica gel chromatography using CHCl3: EtOH 7%: NH4OH 0.7% to afford the title compound as a solid.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07381719B2uspto-grants-2008_06