2-Methyl-8-hydroxyquinoline → 8-Hydroxy-2-quinolinecarboxaldehyde

HRID 623390

Reaction equation

HRID 623390 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2.[O:13]1CCOCC1>>[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH:12]=[O:13])[CH:8]=[CH:7]2

Participants

3

Reactant 2

HCID 132242-Methyl-8-hydroxyquinolineHCID 312751,4-Dioxane2×

Product 1

HCID 5993428-Hydroxy-2-quinolinecarboxaldehydeYield 38%

Conditions

Temperature
80 °C

Procedure

A solution of 8-hydroxy-2-methylquinoline (6.0 g, 37.7 mmol) in dioxane (15 ml) was added to a stirred solution of SeO2 (6.3 g, 56.8 mmol) in dioxane (80 ml) dropwise at 50° C. and the mixture was heated up to 80° C. for further 20 h. The resulting mixture was filtered. The filtrate was concentrated and the residue purified by column chromatography with Hex/EA=(15:1 to 10:1) to give 8-hydroxyquinoline-2-carboxaldehyde (2.45 g, 38%) derivatives as intermediates. Intermediate was converted into N-substituted compounds by reductive amination with aminoalcohol, aminoalkyne or other heterocycles to give series of compounds. 8-alkoxy-2-methyl quinoline were oxidized to give 8-alkoxyquinoline-2-carboxaldehyde derivatives and followed by the same method to give compounds M to O.

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationThe filtrate was concentrated
  3. customthe residue purified by column chromatography with Hex/EA=(15:1 to 10:1)

Sources & evidence

ORD record
ord-8ccab9494bbe4804b713961b03c5e461
Source dataset
uspto-grants-2016_04
Patent number
US09302992B2

Linked notes

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