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<example id="h0302" title="EXAMPLE 130"><heading id="h0303" title="1-Methyl-3-phenylpropyl 8-hydroxyquinoline-7-carboxamide"><p id="p0421" num="0421">
<chemistry id="chem0206" num="0206"><img id="ib0206" file="imgb0206.tif" wi="82" he="27" img-content="chem" img-format="tif" orientation="portrait" inline="no"/></chemistry></p><p id="p0422" num="0422">A mixture of 8-hydroxyquinoline-7-carboxylic acid (0.50 g, 2.64 mmol), 1-methy-3-phenylpropylamine (0.39 g, 2.64 mmol), 1-hydroxybenzotriazole (0.45 g, 2.91 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.50 g, 2.64 mmol), and triethylamine (1.3 mL, 9.25 mmol) in DMF (15 mL) was stirred at room temp overnight. The reaction mixture was concentrated under vacuum. The residue was dissolved in DMSO and subjected to HPLC purification on C-18 stationary phase eluted with water/acetonitrile/TFA mobile phase. Collection and lyophilization of appropriate fractions provide the title compound as yellow solid. <spectrum type="hnmr">1H NMR (<quantity type="frequency"><value><point>400</point></value> <units>MHz</units></quantity>, <quantity type="solvent">DMSO-d6</quantity>) δ <peaks type=".."><peak><quantity type="shift"><value><point>9.01</point></value></quantity> (<quantity type="peaktype">br s</quantity>, <quantity type="integral"><value><point>1</point></value><units>H</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>8.88</point></value></quantity> (<quantity type="peaktype">br s</quantity>, <quantity type="integral"><value><point>1</point></value><units>H</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>8.62</point></value></quantity> (<quantity type="peaktype">br d</quantity>, <quantity type="integral"><value><point>1</point></value><units>H</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>8.17</point></value></quantity> (<quantity type="peaktype">d</quantity>, <quantity type="integral"><value><point>1</point></value><units>H</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>7.84</point></value></quantity> (<quantity type="peaktype">br s</quantity>, <quantity type="integral"><value><point>1</point></value><units>H</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>7.69</point></value></quantity> (<quantity type="peaktype">dd</quantity>, <quantity type="integral"><value><point>1</point></value><units>H</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>7.57</point></value></quantity> (<quantity type="peaktype">d</quantity>, <quantity type="integral"><value><point>1</point></value><units>H</units></quantity>)</peak>, <peak><quantity type="shift"><value><min>7.29</min> - <max>7.17</max></value></quantity> (<quantity type="peaktype">m</quantity>, <quantity type="integral"><value><point>5</point></value><units>H</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>4.14</point></value></quantity> (<quantity type="peaktype">m</quantity>, <quantity type="integral"><value><point>1</point></value><units>H</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>2.66</point></value></quantity> (<quantity type="peaktype">br s</quantity>, <quantity type="integral"><value><point>2</point></value> <units>H</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>1.94</point></value></quantity> (<quantity type="peaktype">br m</quantity>, <quantity type="integral"><value><point>1</point></value><units>H</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>1.85</point></value></quantity> (<quantity type="peaktype">br m</quantity>, <quantity type="integral"><value><point>1</point></value><units>H</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>1.25</point></value></quantity> (<quantity type="peaktype">d</quantity>, <quantity type="integral"><value><point>3</point></value><units>H</units></quantity>)</peak></peaks></spectrum>.</p></heading></example>
