ChemicalBook CAS DataBase List METHYL 6-BROMOQUINOLINE-2-CARBOXYLATE

METHYL 6-BROMOQUINOLINE-2-CARBOXYLATE synthesis

6synthesis methods

Product Name:METHYL 6-BROMOQUINOLINE-2-CARBOXYLATE
CAS Number:623583-88-0
Molecular formula:C11H8BrNO2
Molecular Weight:266.09

67-56-1 Synthesis

67-56-1
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65148-10-9 Synthesis

65148-10-9
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623583-88-0
43 suppliers
$125.00/100mg

Yield: 85%

Reaction Conditions:

Stage #1:methanol;6-bromo-quinoline-2-carboxylic acid with methanesulfonic acid for 6 h;Heating / reflux;
Stage #2: with water;sodium hydrogencarbonate in methanol at 20;

Steps:

1.1c
1c) Methyl 6-bromo-2-quinolinecarboxylate A mixture of 6-bromo-2-quinolinecarboxylic acid (331 g, from multiple batches, 1.31 mol) and methanesulfonic acid (22 mL, 33 g, 0.34 mol) in methanol (2 L) was refluxed for 6 hr. The mixture was treated with a solution of sodium bicarbonate (29 g, 0.34 mol) in water (350 mL) and the resulting suspension was slowly cooled to 20° C. and stirred overnight. The suspension was filtered and the cake was washed with water (1 L). The solid was dried in a vacuum oven at 50° C. for 3 days to yield methyl 6-bromo-2-quinolinecarboxylate (294 g, 85%). 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:

SmithKline Beecham Corporation US2008/96921, 2008, A1 Location in patent:Page/Page column 32