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153437-51-5

5-morpholino-2-nitrobenzenecarboxylic acid synthesis

3synthesis methods
110-91-8 Synthesis
Morpholine

110-91-8
688 suppliers
$9.00/1g

2516-95-2 Synthesis
5-Chloro-2-nitrobenzoic acid

2516-95-2
319 suppliers
$5.00/5g

5-morpholino-2-nitrobenzenecarboxylic acid

153437-51-5
15 suppliers
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Yield:153437-51-5 100%

Reaction Conditions:

Stage #1: morpholine;5-chloro-2-nitrobenzoic acid at 110; for 2 h;Neat (no solvent);
Stage #2: pH=Ca. 3;Acidic aq. solution;

Steps:

8.1.54. 2-Nitro-5-(piperidin-1-yl) benzoic acid (12a)

General procedure: The mixture of 5-chloro-2-nitrobenzoic acid (10 g, 0.05 mol) and piperidine (21.10 g/24.5 mL, 0.25 mol) was stirred at 110 °C for 2 h. The mixture was then cooled, pH of which was adjusted to about 3. The precipitate was collected by filteration and washed by water to gain (12a) as a yellow powder (11.88 g, 95.04%): mp 151-154 °C. The product was used directly in next step without further purification.

References:

Jiang, Cheng;Yang, Lei;Wu, Wu-Tong;Guo, Qing-Long;You, Qi-Dong [Bioorganic and Medicinal Chemistry,2011,vol. 19,# 18,p. 5612 - 5627] Location in patent:experimental part