3-Quinolinecarboxylic acid, 6-broMo-, Methyl ester Chemical Properties

Boiling point:

348.5±22.0 °C(Predicted)

Density 

1.557±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

2.30±0.14(Predicted)

3-Quinolinecarboxylic acid, 6-broMo-, Methyl ester Usage And Synthesis

Synthesis

Example 1: Synthesis of tert-butyl {3-[(hydroxyamino)carbonyl]quinolin-6-yl}carbamate (Compound 1-21, Int-2) Step 1: Synthesis of methyl 6-bromoquinoline-3-carboxylate (Intermediate 1) [00161] To a solution of 6-bromoquinoline-3-carboxylic acid (3 g, 11.9 mmol) in methanol (55 mL) was slowly added concentrated sulfuric acid (0.32 mL, 6 mmol). The reaction mixture was stirred and refluxed at 85 °C for 96 hours. Upon completion of the reaction, the mixture was cooled to room temperature and the pH was adjusted to 7 by slow addition of saturated sodium bicarbonate solution.During neutralization, methyl 6-bromoquinoline-3-carboxylate precipitated as a solid, which was collected by filtration (Intermediate 1, 2.77 g, 97% yield). Product Characterization: LC-MS (FA) ES+ m/z: 266 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm: 9.33 (d, J = 2.1 Hz, 1H), 9.01 (d, J = 2.1 Hz, 1H), 8.53 (t, J = 1.3 Hz, 1H), 8.07-8.01 (m, 2H), 3.95 (s, 3H).

References

[1] Patent: WO2011/146591, 2011, A1. Location in patent: Page/Page column 60
[2] Patent: WO2014/86697, 2014, A1. Location in patent: Page/Page column 46-47

3-Quinolinecarboxylic acid, 6-broMo-, Methyl ester(1220418-77-8)Related Product Information

• ETHYL 6-BROMOQUINOLINE-3-CARBOXYLATE