Reacción #4537

ord-0e6c16dd3649420f8ec300810a013520

Ecuación de reacción

[O]=[Cr](=[O])([O-])[Cl].c1cc[nH+]cc1
pyridinium chlorochromate
O=C1c2ccccc2C(=O)N1c1ncc(C(Cl)Cl)nc1CO
3-hydroxymethyl-5-dichloromethyl-2-phthalimidopyrazine
O=Cc1nc(C(Cl)Cl)cnc1N1C(=O)c2ccccc2C1=O
colorless crystals
Rendimiento 78.0%
O=Cc1nc(C(Cl)Cl)cnc1N1C(=O)c2ccccc2C1=O
3-formyl-5-dichloromethyl-2-phthalimidopyrazine
Rendimiento 78.0%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Filtraciónfiltered over silica gel
  2. 2
    Otrothe filtrate was evaporated down

Procedimiento

5.1 g of pyridinium chlorochromate were added a little at a time to a solution of 4 g of 3-hydroxymethyl-5-dichloromethyl-2-phthalimidopyrazine in 80 ml of dichloromethane at 35° C., after which the mixture was stirred for 40 minutes and filtered over silica gel, and the filtrate was evaporated down. 3.1 g (76%) of colorless crystals of 3-formyl-5-dichloromethyl-2-phthalimidopyrazine of melting point 145°-146° C. (from ethyl acetate) were obtained. 1H-NMR (270 MHz, CDCl3): δ6.9 (s, 1H), 8.0 (m, 4H), 9.3 (s, 1H), 10.1 (s, 1H).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04725689uspto-grants-1988_02