METHYL 6-BROMOQUINOLINE-2-CARBOXYLATE Chemical Properties

Boiling point:

374.6±22.0 °C(Predicted)

Density 

1.557±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

1.18±0.43(Predicted)

Appearance

Off-white to pink Solid

METHYL 6-BROMOQUINOLINE-2-CARBOXYLATE Usage And Synthesis

Synthesis

1c) Synthesis of methyl 6-bromo-2-quinolinecarboxylate A mixture of 6-bromo-2-quinolinecarboxylic acid (331 g, multiple batches, 1.31 mol) and methanesulfonic acid (22 mL, 33 g, 0.34 mol) in methanol (2 L) was refluxed for 6 hours. Upon completion of the reaction, the reaction mixture was neutralized with an aqueous solution of sodium bicarbonate (29 g, 0.34 mol) (350 mL). The resulting suspension was slowly cooled to 20 °C and stirred continuously overnight. The solid product was collected by filtration and the filter cake was washed with water (1 L). The solid product was dried in a vacuum oven at 50 °C for 3 days to give methyl 6-bromo-2-quinolinecarboxylate (294 g, 85% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.52 (d, J = 9 Hz, 1H), 8.40 (d, J = 2 Hz, 1H), 8.14 (d, J = 9 Hz, 1H), 8.08 (d, J = 9 Hz, 1H), 7.97 (m, 1H), 3.93 (s, 3H). ES-LCMS m/z 267 (M + H)+.

References

[1] Patent: US2008/96921, 2008, A1. Location in patent: Page/Page column 32
[2] Tetrahedron, 2014, vol. 70, # 42, p. 7686 - 7690
[3] Patent: WO2011/127643, 2011, A1. Location in patent: Page/Page column 38

METHYL 6-BROMOQUINOLINE-2-CARBOXYLATE(623583-88-0)Related Product Information

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