反応 #56946

反応方程式

4-Fluoro-3-nitrobenzoic acid

aniline

NMM

→

4-anilino-3-nitrobenzoic acid

溶媒

2-methoxyethanol

反応条件

後処理

1. 1
   温度at reflux under argon for 24 h
2. 2
   濃縮The suspension was concentrated under reduced pressure
3. 3
   その他the residue was sonicated with 1M HCl (aq) over 1.5 h
4. 4
   その他The resultant orange solid was isolated by filtration
5. 5
   洗浄washed with water
6. 6
   その他dried
7. 7
   その他sonicated with t-butyl methyl ether
8. 8
   その他isolated by filtration
9. 9
   その他dried
10. 10
    その他Where necessary, the product was further purified by recrystallisation

実験手順

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).

出典