HCID 86732765, compound → HCID 86732766, compound

HRID 525903Notes

Reaction equation

HRID 525903 reaction equation
[Cl:1][C:2]1[C:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[C:10]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:36])[C:5]([CH2:34][OH:35])=[CH:6][N:7]2[CH2:32][CH3:33]>ClCCl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[C:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[C:10]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=2)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:36])[C:5]([CH:34]=[O:35])=[CH:6][N:7]2[CH2:32][CH3:33]

Participants

4

Reactant 1

HCID 86732765HCID 86732765, compound

Product 1

HCID 86732766HCID 86732766, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a yellow solution of 5-chloro-1-ethyl-3-(hydroxymethyl)-6,7-bis((4-methoxybenzyl)oxy) quinolin-4(1H)-one (19 g, 30.9 mmol) in Dichloromethane (DCM) (250 mL) was added manganese dioxide (41.1 g, 402 mmol), and the mixture was stirred at r.t. for overnight. The mixture was then filtered through Celite and washed with DCM. The filtrate was concentrated to afford 5-chloro-1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinoline-3-carbaldehyde (17 g, 27.4 mmol, 89% yield) as a yellow solid, which was used in the next step without further purification. LCMS: (M+H)+: 508.1.

Workup

  1. filtrationThe mixture was then filtered through Celite
  2. washwashed with DCM
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-38acb558916a4ef5850aafa29b10a3d1
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

Loading…