Reacción #465962

ord-fb557ee8ce70414a8c0f135b631c4c2d

Ecuación de reacción

NC(=O)c1nc(Br)c(Br)c(Br)c1Br
3,4,5,6-Tetrabromopyridine-2-carboxamide
N
ammonia
CO
methanol
Nc1cc(Br)nc(C(=O)O)c1Br
4-amino-3,6-dibromopyridine-2-carboxylic acid

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    ConcentraciónThe resultant solution was concentrated to an off-white solid and hydrolyzed with conc. sulfuric acid (25 mL) at 140° C. for 3 hr
  2. 2
    Extracciónextracted with EtOAc (2×100 mL)
  3. 3
    Filtraciónfiltered

Procedimiento

3,4,5,6-Tetrabromopyridine-2-carboxamide (5.0 g) was selectively aminated with ammonia gas at RT in 100 mL methanol. The resultant solution was concentrated to an off-white solid and hydrolyzed with conc. sulfuric acid (25 mL) at 140° C. for 3 hr. the mixture was made basic with NaOH, extracted with EtOAc (2×100 mL), acidified and filtered to give 1.4 g of pure 4-amino-3,6-dibromopyridine-2-carboxylic acid; mp 205° C. dec.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US06297197B1uspto-grants-2001_10