Reacción #502105

ord-a83387cdb3d04fc18f5c12294af90f82

Ecuación de reacción

O=C(O)c1ccnc(Br)c1
2-bromoisonicotinic acid
CNOC.Cl
N,O-dimethylhydroxylamine hydrochloride
CCN=C=NCCCN(C)C
1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide
c1ccncc1
pyridine
CON(C)C(=O)c1ccnc(Br)c1
compound
Rendimiento 82.4%
CON(C)C(=O)c1ccnc(Br)c1
2-Bromo-N-methoxy-N-methylisonicotinamide
Rendimiento 82.4%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    ConcentraciónThe mixture is concentrated
  2. 2
    LavadoThe organic phase is washed with 50 ml of a 1N solution of sodium hydroxide and 50 ml of a saturated solution of sodium chloride
  3. 3
    Secadodried over magnesium sulphate
  4. 4
    Concentraciónconcentrated under reduced pressure

Procedimiento

In a round-bottomed flask, 2.0 g of 2-bromoisonicotinic acid, 1.1 g of N,O-dimethylhydroxylamine hydrochloride, 3.8 g of 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide and 3.2 ml of pyridine are placed in 50 ml of tetrahydrofuran. The mixture is stirred at ambient temperature for 40 h. The mixture is concentrated, and the residue is taken up in 50 ml of ethyl acetate and 50 ml of water. The organic phase is washed with 50 ml of a 1N solution of sodium hydroxide and 50 ml of a saturated solution of sodium chloride, dried over magnesium sulphate and then concentrated under reduced pressure. 2.0 g of compound are obtained.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08088765B2uspto-grants-2012_01