Reacción #47737

ord-ff5b7f31a9314cb5b8450f6baebb601a

Ecuación de reacción

O=C1CCCC(=O)O1
Glutaric anhydride
C#Cc1ccc(N)cc1
p-aminophenyl-acetylene
C#Cc1ccc(NC(=O)CCCC(=O)O)cc1
yellow white product 24
Rendimiento 96.0%
C#Cc1ccc(NC(=O)CCCC(=O)O)cc1
4-(4-Ethynyl-phenylcarbamoyl)-butyric acid
Rendimiento 96.0%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrowas evaporated under reduced pressure

Procedimiento

Glutaric anhydride (540 mg, 4.70 mmol) was dissolved in anhydrous dichloromethane (7 mL) and followed with the addition of p-aminophenyl-acetylene (500 mg, 4.27 mmol). The mixture was allowed to stir at room temperature for 6 hours before the solvent was evaporated under reduced pressure to provide 900 mg of a yellow white product 24 (96%); mp 135-140° C.; 1H NMR (DMSO-d6, 300 MHz) δ 1.77 (p, J=8.21 Hz, 2H), 2.25 (t, J=9.30 Hz, 2H), 2.34 (t, J=6.56 Hz, 2H), 4.05 (s, 1H), 7.38 (d, J=8.52 Hz, 2H), 7.59 (d, J=7.91 Hz, 2H) 9.90 (s, 1H); HRMS m/e calculated for (M+H)+: C13H13NO3 231.0895; found 231.0895.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07745229B2uspto-grants-2010_06