ChemicalBook CAS DataBase List 7-BROMOQUINOLIN-2(1H)-ONE

7-BROMOQUINOLIN-2(1H)-ONE synthesis

5synthesis methods

Product Name:7-BROMOQUINOLIN-2(1H)-ONE
CAS Number:99465-10-8
Molecular formula:C9H6BrNO
Molecular Weight:224.05

99455-15-9

99465-10-8

The general procedure for the synthesis of 7-bromo-2-chloroquinolin-2(1H)-one from 7-bromo-2-chloroquinoline was as follows: 7-bromo-2-chloroquinoline (5.0 g, 20.6 mmol) was dissolved in a mixed solvent of 5 M aqueous hydrochloric acid (133 mL) and 1,4-dioxane (14 mL) with stirring and heated to reflux for 2 hours. After completion of the reaction, it was cooled to room temperature, the precipitate precipitated was collected by filtration and washed with deionized water to afford 7-bromoquinolin-2(1H)-one as a colorless solid (4.3 g, 93% yield). The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 11.80 (s, 1H), 7.91 (d, J=8.0 Hz, 1H), 7.63 (d, J=8.0 Hz, 1H), 7.48 (d, J=8.0 Hz, 1H), 7.34 (dd, J=8.0, 4.0 Hz, 1H), 6.53 (d, J= 4.0 Hz, 1H).

99455-15-9 Synthesis

99455-15-9
134 suppliers
$12.00/100mg

99465-10-8
115 suppliers
$22.00/100mg

Yield:99465-10-8 93%

Reaction Conditions:

with hydrogenchloride in 1,4-dioxane;water for 2 h;Reflux;

Steps:

14.i 7-Bromoquinolin-2(1H)-one
A stirred solution mixture of 7-bromo-2-chloroquinoline (5.0 g, 20.6 mmol) in 5 M aqueous hydrochloric acid (133 mL) and 1,4-dioxane (14 mL) was heated at reflux for 2 h. The reaction was cooled and the resulting precipitate was collected by filtration and washed with water to afford the subtitled compound as a colourless solid (4.3 g, 93%). ¹H NMR (400 MHz, DMSO-d₆): δ 11.80 (s, 1H), 7.91 (d, 1H), 7.63 (d, 1H), 7.48 (d, 1H), 7.34 (dd, 1H), 6.53 (d, 1H).

References:

ASTRAZENECA AB;LONN, Hans Roland;CONNOLLY, Stephen;SWALLOW, Steven;KARLSSON, Staffan PO;AURELL, Carl-Johan;PONTéN, John Fritiof;DOYLE, Kevin James;VAN DE PO?L, Amanda Jane;JONES, Graham Peter;WATSON, David Wyn;MACRITCHIE, Jaqueline Anne;PALMER, Nicholas John US2015/210655, 2015, A1 Location in patent:Paragraph 0291

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