3-NITRO-4-QUINOLINOL

Tan Solid

3-nitro-1H-quinolin-4-one is a nitro compound and a member of quinolines.

The first step: 5 g of 4-hydroxyquinoline of formula VI-1 (34.48 mmol, Purchased from Jiuding Chemical) dissolved in propionic acid (40mL, purity ≥99.5percent) and heated to 120°C; then, 3.5 mL of concentrated nitric acid diluted with propionic acid (41.38 mmol, The concentration of concentrated nitric acid is 65-68percent) slowly dropping in 1.5h, after about 15min, there is a yellow precipitate; Adding 20 mL of propionic acid followed by refluxing for 1 h. TLC (thin-layer chromatography) showed no 4-hydroxyquinoline as a reactant. The heating was stopped and the reaction solution was cooled to room temperature. The reaction solution was filtered, and the filter cake was washed with petroleum ether and vacuum-dried. The resulting yellow solid is 4-hydroxy-3-nitroquinoline of Formula V-1 (5.28 g, average yield 80.7percent), 4-Hydroxyquinoline (79.3 g) and propionic acid (790 mL) were combined and heated to 125° C. Nitric acid (79 mL) was added dropwise over 40 minutes. The reaction mixture was stirred at reflux temperature for a further 3 h and cooled to rt. The mixture was diluted with ethanol and the solid was collected by vacuum filtration. The solid was washed with ethanol, water then ethanol. The residue was refluxed in ethanol and the hot mixture was filtered and dried to give the subtitle compound (80.9 g). Yield: 76percentEXAMPLE 15: Into a 1 00-mL round-bottom flask was placed a solution of quinolin-4-ol (4 g, 27.56 mmol, 1.00 equiv) in CH3CH2COOH (30 mL). This was followed by the additionof HNO3 (1.77 mL). The resulting solution was stirred overnight at 125°C in an oil batch. The reaction mixture was cooled to room temperature and poured into water/ice. Theprecipitated solid was collected by filtration, washed with water and ethanol, and dried. This resulted in 3.414 g (65percent) of 3-nitroquinolin-4-ol as a yellow solid.LC-MS: (ES, m/z): [M+H] = 191.070percent Aqueous nitric acid (6.1 mL) was added dropwise to a mixture of 4- hydroxyquinoline (10 g, 69 mmol) and 100 mL of acetic acid heated at reflux. After 15 min, the mixture was allowed to cool to room temperature. Dilution with EtOH resulted in the formation of a precipitate, which was filtered and washed sequentially with EtOH, H3-Nitro-4-hydroxyquinoline (compound 5); Compound 5 was prepared as described elsewhere [Bachman, G. B. et al. Quinoline Derivatives from 3-Nitro-4-hydroxyquinoline, J. Am. Chem. Soc, 1947, 69, 365-371]. In brief, a mixture of 2-β-mtroethylideaminobenzoic acid 3 (10.4 g, 50 mmol) and technical acetic anhydride (50 ml) was placed in a 3-necked flask of at least 100 mL capacity fitted with thermometer, magnetic stirrer and reflux condenser. It was stirred and heated to 100-105

Molecular Weight:190.16
XLogP3:1.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Exact Mass:190.03784206
Monoisotopic Mass:190.03784206
Topological Polar Surface Area:74.9
Heavy Atom Count:14
Complexity:306
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes