Reaktion #89921

Reaktionsgleichung

4-methoxy-5-benzyloxy-2-nitrobenzamide

→

4-methoxy-5-benzyloxy-2-aminobenzamide

Ausbeute 87.2%

Lösungsmittel

acetic acid methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool to RT
2. 2
   Sonstigethe iron was removed by filtration, and volatiles
3. 3
   Sonstigewere removed in vacuo
4. 4
   Extraktionthe mixture was extracted with ethyl acetate (600 mL×3)
5. 5
   WaschenThe combined organic layers were washed with water (1×150 mL), brine (1×150 mL)
6. 6
   Trocknendried (Na2SO4)
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated in vacuo

Vorschrift

A mixture of 4-methoxy-5-benzyloxy-2-nitrobenzamide (6.60 g, 21.9 mmol) and iron powder (8.14 g, 0.146 mol) in acetic acid/methanol (80 mL/80 mL) was heated at 85±5° C. for 1.5 h. The reaction mixture was allowed to cool to RT and the iron was removed by filtration, and volatiles were removed in vacuo. The residue was taken up in sat. sodium bicarbonate and the mixture was extracted with ethyl acetate (600 mL×3). The combined organic layers were washed with water (1×150 mL), brine (1×150 mL), dried (Na2SO4), filtered and concentrated in vacuo to give 4-methoxy-5-benzyloxy-2-aminobenzamide (5.2 g, 19.1 mmol, 87%). MS 273.2. (M+). HPLC retention time 4.585 min.

Quelle