[8-Chloro-2-(pyridin-3-yl)quinolin-3-yl]methanol → 8-Chloro-2-(pyridin-3-yl)quinoline-3-carbaldehyde

HRID 572123Notes

Reaction equation

HRID 572123 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)[C:8]([CH2:18][OH:19])=[CH:7]2>ClC1C=CC=CC=1.O=[Mn]=O>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)[C:8]([CH:18]=[O:19])=[CH:7]2

Participants

4

Reactant 1

HCID 66691162[8-Chloro-2-(pyridin-3-yl)quinolin-3-yl]methanol

Product 1

HCID 867011658-Chloro-2-(pyridin-3-yl)quinoline-3-carbaldehydeYield 86.3%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 7964ChlorobenzeneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of [8-chloro-2-(pyridin-3-yl)quinolin-3-yl]methanol (0.6 g, 2.2 mmol) and MnO2 (1.0 g) in chlorobenzene (30 mL) was heated at 70° C. overnight, filtered through a celite plug, concentrated in vacuo and washed with DCM to give the title compound (510 mg, 86%) as a white solid.

Workup

  1. filtrationfiltered through a celite plug
  2. concentrationconcentrated in vacuo
  3. washwashed with DCM

Sources & evidence

ORD record
ord-bd499a79d24743db8d495e4983418023
Source dataset
uspto-grants-2015_05
Patent number
US09029392B2

Reaction notes

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