HCID 86732818, compound → HCID 86732820, compound

HRID 525951Notes

Reaction equation

HRID 525951 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)[C:11]=2[O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[C:6](=[O:33])[C:5]([CH2:34][OH:35])=[CH:4]1)[CH3:2]>ClCCl.[O-2].[O-2].[Mn+4]>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:23][CH2:24][C:25]3[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=3)[C:11]=2[O:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)[C:6](=[O:33])[C:5]([CH:34]=[O:35])=[CH:4]1)[CH3:2]

Participants

4

Reactant 1

HCID 86732818HCID 86732818, compound

Product 1

HCID 86732820HCID 86732820, compoundYield 62.9%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a yellow solution of 1-ethyl-3-(hydroxymethyl)-7,8-bis((4-methoxybenzyl)oxy)quinolin-4(1H)-one (16 g, 33.6 mmol) in Dichloromethane (DCM) (200 mL) was added manganese dioxide (29.3 g, 336 mmol), and the mixture was stirred at rt for 6.5 h. The mixture was filtered through Celite and washed with DCM, the filtrate was concentrated to afford 1-ethyl-7,8-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinoline-3-carbaldehyde (10 g, 21.12 mmol, 62.8% yield) as a brown solid, which was used in the next step without further purification. LCMS: (M+H)+: 474.3.

Workup

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

Sources & evidence

ORD record
ord-913cbb89a1e44ba5804a4556734ea583
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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