Benzyl‐ und Allyl‐triethylammonium‐Salze (I) liefern bei Belichtung (350 11m) und in Gegenwart von Dicobaltoctacarbonyl und Alkali die Carbonsäuren (II) in z.Tl. recht hohen Ausbeuten.
General Procedure for the Preparation of 2-Cyanoquinolines: 2-Cyano-6-methoxyquinoline (8b). A mixture of 6-meth0xyquinoline (11.1 g, 70.0 mmol) in CH2C12 (140 mL) and H20 (40 mL) containing KCN (13.70 g, 210 mmol, 3.0 equiv) was treated dropwise (30 min) with a solution of p-toluenesulfonyl chloride (p-TsCl; 22.0 g, 115.0 mmol, 1.6 equiv) in CH2C12 (150 mL) at 25 °C. After being stirred for 120 h at 25 °C, the mixture was filtered through Celite (washed with CH2C12,4 x 30 mL) and the filtrate was concentrated in vacuo. The crude product was dissolved in CHC13 and passed through a plug of Si02 (CHC13 eluant). The combined CHC13 fractions were concentrated in vacuo and the product was recrystallized from ethanol-water, affording 10.40 g (12.81 g theoretical, 81%) of pure 8b: mp 175-176 °C (ethanol-water) (lit.3 mp 177-178 °C); NMR (CDC13) b 8.
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