4-HYDROXY-7-NITROQUINOLINE-3-CARBOXYLIC ACID synthesis
- Product Name:4-HYDROXY-7-NITROQUINOLINE-3-CARBOXYLIC ACID
- CAS Number:40107-11-7
- Molecular formula:C10H6N2O5
- Molecular Weight:234.16
7248-88-6
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Yield:40107-11-7 88%
Reaction Conditions:
with sodium hydroxide in lithium hydroxide monohydrate; for 0.75 h;Reflux;
Steps:
4-hydroxy-7-nitroquinoline-3-carboxylic acid (5h)
4h (5.28 g; 20.15 mmol) was suspended in 2 M NaOH (80 mL) and refluxed at 110 °C for 45 minutes. Progress of the reaction was monitored by solubilization of the product. The mixture was cooled to room temperature and acidified (pH 3-4) with 2 M HCl. The precipitate was filtered, washed with water and dried to give 5h (4.13 g, 88%) as a brown solid, mp 265-267 °C (lit. Vippagunta et al 1999, 274 - 275 °C).1 δH (400 MHz; DMSO) 8.27 (1H, dd, J 2.2, 8.9 Hz, H-6), 8.51 (1H, d, J 8.9 Hz, H-5), 8.68 (1H, d, J 2.1 Hz, H-8), 9.04 (1H, s, H-2). δC (100 MHz; DMSO) 109.8 (C-3), 116.1 (C-8), 119.8 (C-4a), 123.1 (C-6), 128.1 (C-5), 146.2 (C-8a), 147.3 (C-2), 150.6 (C-7), 165.9 (C-4), 178.0 (COOH).
References:
Nsumiwa, Samkele;Kuter, David;Wittlin, Sergio;Chibale, Kelly;Egan, Timothy J. [Bioorganic and Medicinal Chemistry,2013,vol. 21,# 13,p. 3738 - 3748] Location in patent:supporting information
40107-10-6
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99-09-2
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