ChemicalBook CAS DataBase List 6-Bromo-3-nitro-4-quinolinol

6-Bromo-3-nitro-4-quinolinol synthesis

9synthesis methods

Product Name:6-Bromo-3-nitro-4-quinolinol
CAS Number:853908-50-6
Molecular formula:C9H5BrN2O3
Molecular Weight:269.05

Benzoic acid, 5-broMo-2-[[(1E)-2-nitroethenyl]aMino]-

1201643-75-5

853908-50-6

5-Bromo-2-(2-nitrovinylamino)benzoic acid (25 g, 87 mmol) was used as starting material, which was mixed with acetic anhydride (10.5 mL, 104 mmol) in acetic acid anhydride (112 mL, 1185 mmol), and the reaction was stirred for 3 hr at 120° C. The reaction was completed by filtration. After completion of the reaction, the precipitate was collected by filtration and washed with acetic acid until the filtrate was colorless. The precipitate was subsequently washed with water and dried to give the target product 6-bromo-4-hydroxy-3-nitroquinoline. Yield: 15 g (64%). The structure of the product was confirmed by 1H NMR (CDCl3, 500MHz): δ 9.275 (s, 1H), 8.611-8.615 (d, 1H, J = 2Hz), 8.100-8.118 (d, 1H, J = 9Hz), 8.026-8.048 (dd, 1H, J = 8.5Hz, 2Hz).

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Yield:853908-50-6 64.5%

Reaction Conditions:

with nitric acid;propionic acid for 2 h;

Steps:

1.D Step D 3-Nitro-4-hydroxy-6-bromoquinoline (4a)

Synthesis of Compound 3a (29.0 g, 0.130 mol)Add to a 500 mL three-necked flask,Heat and stir until dissolved.Further, a mixture of nitric acid (40.95 g, 0.650 mol) and propionic acid (10 mL) was slowly added dropwise to the reaction flask.After the addition is completed, the reaction is further carried out for 2 hours.TLC detection [V (dichloromethane): V (methanol) = 15:1] The reaction was completed, cooled, filtered,The filter residue is added to the ice saturated sodium bicarbonate solution and stirred.Filtered,The residue is dry,The compound was obtained as a yellow solid (26.0 g, yield: 64.5%).

References:

CN108456165,2018,A Location in patent:Paragraph 0047; 0079-0080

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References

853908-49-3 Synthesis