Reacción #325376

ord-93282f27c7324c43b9574405a79f830f

Ecuación de reacción

CCc1nc2ccccc2c(=O)o1
2-ethyl-benzo[d][1,3]oxazin-4-one
CCCN
propylamine
CCCn1c(CC)nc2ccccc2c1=O
product
Rendimiento 29.1%
CCCn1c(CC)nc2ccccc2c1=O
2-Ethyl-3-propyl-3H-quinazolin-4-one
Rendimiento 29.1%

Condiciones de reacción

Temperatura
110°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe crude product was purified by column chromatography (10-40% ethyl acetate-hexanes)

Procedimiento

A mixture of 2-ethyl-benzo[d][1,3]oxazin-4-one (541 mg, 3.1 mmol) and propylamine (254 μL, 3.1 mmol) were heated to 110° C. for 1 hour. The crude product was purified by column chromatography (10-40% ethyl acetate-hexanes) to yield the product as a white solid (195 mg, 29%). 1H NMR (CDCl3) δ 1.03 (t, 3H, J=7.4 Hz), 1.41 (t, 3H, J=7.3 Hz), 1.76 (sex, 2H, J=7.7 Hz), 2.86 (q, 2H, J=7.4 Hz), 4.05 (t, 2H, J=7.9 Hz), 7.42 (t, 1H, J=8.1 Hz), 7.63 (d, 1H, J=7.7 Hz), 7.70 (t, 1H, J=7.7 Hz), 8.24 (d, 1H, J=8.1 Hz).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08642609B2uspto-grants-2014_02