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<example id="h0155" title="EXAMPLE 70"><heading id="h0156" title="5-benzenesulfonyl-8-hydroxy-[1,6]naphthyridine-7-carboxylic acid 3,5-dichlorobenzylamide"><p id="p0281" num="0281">
<chemistry id="chem0146" num="0146"><img id="ib0146" file="imgb0146.tif" wi="74" he="45" img-content="chem" img-format="tif" orientation="portrait" inline="no"/></chemistry></p><p id="p0282" num="0282">To a 25 mL round bottomed flask with a stirring bar was added 8-hydroxy-5-phenylsulfanyl-[1,6]naphthyridine-7-carboxylic acid 3,5-dichlorobenzylamide (0.04g, 0.09 mmol) and methanol (7 mL). To this well stirred solution was added a solution of Oxone® (DuPont trademark; potassium peroxymonosulfate) (0.184g, 0.30 mmol) in water (2 mL). The resulting mixture was stirred vigorously at ambient temperature 20h. The solvents were removed <i>in vacuo</i> and the residue was triturated with water (10 mL) for 30 min. The solid was collected by filtration on a frit. This material was purified by reverse phase chromatography using water/acetonitrile as eluant to give 5-benzenesulfonyl-8-hydroxy-[1,6]naphthyridine-7-carboxylic acid 3,5-dichloro-benzylamide as a solid.<br/>
<spectrum type="hnmr">1H NMR (<quantity type="solvent">CDCl3</quantity>, <quantity type="frequency"><value><point>300</point></value><units>MHz</units></quantity>) δ <peaks type=".."><peak><quantity type="shift"><value><point>9.43</point></value></quantity> (<quantity type="integral"><value><point>1</point></value><units>H</units></quantity>, <quantity type="peaktype">d</quantity>, J=<quantity type="coupling"><value><point>9</point></value><units>Hz</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>9.26</point></value></quantity> (<quantity type="integral"><value><point>1</point></value><units>H</units></quantity>, <quantity type="peaktype">d</quantity>, J=<quantity type="coupling"><value><point>2</point></value><units>Hz</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>9.01</point></value></quantity> (<quantity type="integral"><value><point>2</point></value><units>H</units></quantity>, <quantity type="peaktype">d</quantity>, J=<quantity type="coupling"><value><point>9</point></value><units>Hz</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>7.82</point></value></quantity> (<quantity type="integral"><value><point>1</point></value><units>H</units></quantity>, <quantity type="peaktype">dd</quantity>, J=<quantity type="coupling"><value><point>4</point></value>, <value><point>9</point></value><units>Hz</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>7.58</point></value></quantity> (<quantity type="integral"><value><point>3</point></value><units>H</units></quantity>,<quantity type="peaktype">m</quantity>)</peak>, <peak><quantity type="shift"><value><point>7.48</point></value></quantity> (<quantity type="integral"><value><point>1</point></value><units>H</units></quantity>,<quantity type="peaktype">s</quantity>)</peak> <peak><quantity type="shift"><value><point>7.30</point></value></quantity> (<quantity type="integral"><value><point>4</point></value><units>H</units></quantity>,<quantity type="peaktype">s</quantity>)</peak>, <peak><quantity type="shift"><value><point>7.10</point></value></quantity> (<quantity type="integral"><value><point>1</point></value><units>H</units></quantity>,<quantity type="peaktype">s</quantity>)</peak>, <peak><quantity type="shift"><value><point>4.48</point></value></quantity> (<quantity type="integral"><value><point>2</point></value><units>H</units></quantity>, <quantity type="peaktype">d</quantity>, J=<quantity type="coupling"><value><point>6</point></value><units>Hz</units></quantity>)</peak></peaks></spectrum>.<br/>
FAB MS calc'd for C<sub>22</sub>H<sub>15</sub>Cl<sub>2</sub>N<sub>3</sub>O<sub>4</sub>S 488 (MH<sup>+</sup>), found 488.<br/>
FAB HRMS exact mass calc'd for C<sub>22</sub>H<sub>15</sub>Cl<sub>2</sub>N<sub>3</sub>O<sub>4</sub>S 488.0233 (MH<sup>+</sup>), found 488.0239.</p></heading></example>
