反応 #89920

反応方程式

oxalyl chloride

4-methoxy-5-benzyloxy-2-nitrobenzoic acid

water

ammonium hydroxide

→

4-methoxy-5-benzyloxy-2-nitrobenzamide

収率 65.0%

溶媒

THF

反応条件

後処理

1. 1
   その他A solid was separated out
2. 2
   ろ過which was collected by filtration
3. 3
   その他dried under vacuo
4. 4
   温度in refluxing methanol (500 mL)
5. 5
   ろ過the insoluble solid was collected via filtration
6. 6
   その他dried under vacuum

実験手順

To a suspension of 4-methoxy-5-benzyloxy-2-nitrobenzoic acid (10.0 g, 33.3 mmol) in anhydrous THF (100 mL) was added oxalyl chloride (4.90 mL, 56.2 mmol) followed by one drop of anhydrous DMF. The mixture was stirred at RT for 16 h, upon which the mixture was poured into water (300 mL) and ammonium hydroxide (50 mL). A solid was separated out, which was collected by filtration and dried under vacuo. The solid was taken up in refluxing methanol (500 mL) and the insoluble solid was collected via filtration and dried under vacuum to give 4-methoxy-5-benzyloxy-2-nitrobenzamide (6.50 g, 21.5 mmol, 65%). HPLC retention time 6.154 min.

出典