Selenium Dioxide → 7-Chloroquinoline-4-carbaldehyde

HRID 1743016

Reaction equation

HRID 1743016 reaction equation
[Se](=O)=[O:2].[Cl:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([CH3:15])=[CH:10][CH:11]=[N:12]2)=[CH:7][CH:6]=1>O1CCOCC1.O>[Cl:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([CH:15]=[O:2])=[CH:10][CH:11]=[N:12]2)=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 24007Selenium DioxideHCID 1704377-Chloro-4-methylquinoline

Product 1

HCID 218232177-Chloroquinoline-4-carbaldehydeYield 74.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
85 °C

Procedure

Selenium dioxide (4.52 g; 40.3 mmol) in a mixture of 25 ml of dioxane and 6 ml of water was added in a dropwise fashion to 7-chlorolepidine (6; 6.50 g; 36.6 mmol) in 25 ml of dioxane to 65°-75° C. The temperature was raised to 85° C. and maintained there with stirring for 6 hours. After cooling, the-mixture was filtered through Celite™ and concentrated. The crude material was purified on a flash column, eluting with 10% ethyl acetate/hexane to obtain 5.24 g (74%) of aldehyde 7 as a yellow solid. 1H NMR (CDCl3): δ 7.68 (d, 1H); 7.79 (d, 1H); 8.19 (d, 1H); 9.01 (dd, 1H); 9.21 (m, 1H); 10.45 (s, 1H). IR (KBr): 1702, 1499, 1216, 1041, 900, 653 cm-1.

Workup

  1. temperaturemaintained there
  2. temperatureAfter cooling
  3. filtrationthe-mixture was filtered through Celite™
  4. concentrationconcentrated
  5. customThe crude material was purified on a flash column
  6. washeluting with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-e3cd8f95a6984d3d9e77aaf39f2c4fb7
Source dataset
uspto-grants-1994_08
Patent number
US05342946

Linked notes

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