反应详情

A suspension of 2,5-dibromo-3-nitrobenzoic acid (10.76 g, 0.0331 mol) in toluene (100 mL) was placed under argon, treated with 2-chlorobenzylamine (14.06 g, 0.0993 mol) and the mixture was brought to reflux. A clear, red solution resulted and the solution was refluxed for 24 hours, cooled, poured into 5% sodium hydroxide solution (600 mL) and ether (100 mL). The insoluble material was filtered off, the layers separated and the aqueous phase was added to the insoluble material and acidified with 10% hydrochloric acid solution. The separated crystalline product was collected, washed with water and the solid was crystallized from a large volume of methanol to provide 7.85 g (61.5%) of the yellow crystalline 5-bromo-2-[(2-chlorophenyl)methyl]amino-3-nitrobenzoic acid; mp 159-161° C.

1. temperatureto reflux
2. customA clear, red solution resulted
3. temperaturethe solution was refluxed for 24 hours
4. temperaturecooled
5. filtrationThe insoluble material was filtered off
6. customthe layers separated
7. additionthe aqueous phase was added to the insoluble material
8. customThe separated crystalline product was collected
9. washwashed with water
10. customthe solid was crystallized from a large volume of methanol