Reaktion #9061

Reaktionsgleichung

2-nitroaniline

methyl 4-chlorocarbonyl benzoate

pyridine

→

(2-nitrophenyl)-terephthalamic acid methyl ester

Ausbeute 78.0%

Lösungsmittel

sodium bicarbonate

EtOAc

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe phases separated
2. 2
   Extraktionthe aqueous phase extracted with EtOAc (2×10 mL)
3. 3
   TrocknenThe combined organic extracts were dried (Na2SO4)
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated under reduced pressure

Vorschrift

A solution of 2-nitroaniline (0.41 g, 3.0 mmol) and methyl 4-chlorocarbonyl benzoate (0.65 g, 3.3 mmol) in THF (3.7 mL) and pyridine (0.8 mL) was stirred for 2 h at room temperature. The reaction was diluted with saturated sodium bicarbonate (10 mL) and EtOAc (15 mL), the phases separated and the aqueous phase extracted with EtOAc (2×10 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure to afford (2-nitrophenyl)-terephthalamic acid methyl ester as a yellow solid (0.70 g, 78%). 1H NMR (CDCl3) δ 3.97 (s, 3H), 7.25 (t, 1H, J=7.8 Hz), 7.74 (t, 1H, J=7.8 Hz), 8.04 (d, 2H, J=7.8 Hz), 8.20 (s, 1H (NH)), 8.20 (d, 2H, J=7.8 Hz), 8.30 (d, 1H, J=7.8 Hz), 8.99 (d, 1H, J=7.8 Hz).

Quelle