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ChemicalBook CAS DataBase List 4-Chloroquinoline-6-carbaldehyde
676256-25-0

4-Chloroquinoline-6-carbaldehyde synthesis

6synthesis methods
Quinoline, 4-chloro-6-ethenyl-

916811-99-9
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4-Chloroquinoline-6-carbaldehyde

676256-25-0
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Yield:676256-25-0 84%

Reaction Conditions:

with 2,6-dimethylpyridine;sodium periodate;osmium(VIII) oxide in 1,4-dioxane;water;tert-butyl alcohol at 20; for 2 h;

Steps:

5.b

solution of the compound from Example 5a) (5.36 g, 28.35 mmol) in dioxane (15.0 ml.) and water (5.0 ml.) was treated with osmium tetroxide (7.1 ml_, 2.5% soln. in f-BuOH, 0.57 mmol), 2, 6-lutidine (6.6 ml_, 56.7 mmol), and sodium periodate (24.3 g, 113.4 mmol). After stirring 2 hours at ambient temperature, the reaction was quenched with water, extracted twice with CH2CI2, dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification via flash column chromatography (0-100% ethyl acetate in hexanes) provided the title compound as a white solid (4.5 g, 84%). MS(ES+) m/e 192 [M+H]+. 1 H NMR (400 MHz, CHLOROFORM-d) δ ppm 10.27 (s, 1 H) 8.93 (d, J=4.55 Hz, 1 H) 8.77 (s, 1 H) 8.19 - 8.34 (m, 2 H) 7.62 (d, J=4.80 Hz, 1 H).

References:

WO2007/103756,2007,A2 Location in patent:Page/Page column 50-51

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