5,7-Dichloro-8-hydroxy-2-methylquinoline → 5,7-Dichloro-8-hydroxyquinoline-2-carbaldehyde

HRID 872234Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]([OH:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:14])=[N:7]2.[Se](=O)=[O:16]>O1CCOCC1>[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]([OH:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH:14]=[O:16])=[N:7]2

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 5,7-dichloro-2-methyl-quinolin-8-ol 16 (1.5 g, 6.58 mmol) in 1,4-dioxane (20 mL) was added dropwise over 3 h to a stirred suspension of selenium dioxide (1.3 g, 11.72 mmol) in 1,4-dioxane (60 mL) at 50-55° C. The resulting mixture was then heated at 80° C. overnight, cooled, and the solids filtered off (celite). The filtrate was concentrated and the residue, after washing with diethyl ether (10 mL×3), gave 17 as a yellow solid (quantitative yield). This material was used in the subsequent step without further purification. 1H NMR (CDCl3, 400 MHz): δ 10.26 (s, 1 H), 8.69 (d, J=8.8, 1 H), 8.37 (br, 1 H), 8.17 (d, J=8.8, 1 H), 7.76 (s, 1 H).

Workup

temperaturecooled
filtrationthe solids filtered off (celite)
concentrationThe filtrate was concentrated
washthe residue, after washing with diethyl ether (10 mL×3)

Sources & evidence

ORD record: ord-3ea89c16d7174b60a19ae5310515dbaa
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975278B2

Reaction notes

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