반응 #56946
ord-117d740f4ce941b198f1a4abcf68544e
반응 조건
상세 조건
See reaction.notes.procedure_details.
후처리
- 1온도at reflux under argon for 24 h
- 2농축The suspension was concentrated under reduced pressure
- 3기타the residue was sonicated with 1M HCl (aq) over 1.5 h
- 4기타The resultant orange solid was isolated by filtration
- 5세척washed with water
- 6기타dried
- 7기타sonicated with t-butyl methyl ether
- 8기타isolated by filtration
- 9기타dried
- 10기타Where necessary, the product was further purified by recrystallisation
실험 절차
4-Fluoro-3-nitrobenzoic acid (0.27 mol), an aniline (0.32 mol) and NMM (32.5 mL) in 2-methoxyethanol (750 mL) were stirred at reflux under argon for 24 h. The suspension was concentrated under reduced pressure and the residue was sonicated with 1M HCl (aq) over 1.5 h. The resultant orange solid was isolated by filtration, washed with water dried, then sonicated with t-butyl methyl ether, isolated by filtration and dried. Where necessary, the product was further purified by recrystallisation to yield the 4-anilino-3-nitrobenzoic acid: e.g. 4-(3-bromophenyl amino)-3-nitrobenzoic acid. (In some cases, for example with heteroaromatic anilines, NMN may be omitted from the reaction mixture).