Reacción #502103

ord-d6021ef64e2b49c0bc964dc7747babf1

Ecuación de reacción

O=C(O)c1ccc2cc[nH]c2c1
indole-6-carboxylic acid
CNOC.Cl
N,O-dimethylhydroxylamine hydrochloride
CCN=C=NCCCN(C)C
1-(3-dimethylaminopropyl)-3-ethylcarbodiimide
c1ccncc1
pyridine
CON(C)C(=O)c1ccc2cc[nH]c2c1
compound
Rendimiento 107.3%
CON(C)C(=O)c1ccc2cc[nH]c2c1
N-Methoxy-N-methylindole-6-carboxamide
Rendimiento 107.3%

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, 5.0 g of indole-6-carboxylic acid, 3.3 g of N,O-dimethylhydroxylamine hydrochloride, 11.9 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide and 10 ml of pyridine are placed in 150 ml of tetrahydrofuran. The mixture is stirred at ambient temperature for 40 h. The mixture is concentrated, and the residue is taken up in 150 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. 6.8 g of compound are obtained.

Fuente

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