HCID 86732807, compound → HCID 86732808, compound

HRID 525939Notes

Reaction equation

HRID 525939 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[C:8]([F:33])[C:9]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)=[C:10]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH:11]=2)[C:6](=[O:34])[C:5]([CH2:35][OH:36])=[CH:4]1)[CH3:2]>ClCCl.[O-2].[O-2].[Mn+4]>[CH2:1]([N:3]1[C:12]2[C:7](=[C:8]([F:33])[C:9]([O:23][CH2:24][C:25]3[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=3)=[C:10]([O:13][CH2:14][C:15]3[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=3)[CH:11]=2)[C:6](=[O:34])[C:5]([CH:35]=[O:36])=[CH:4]1)[CH3:2]

Participants

4

Reactant 1

HCID 86732807HCID 86732807, compound

Product 1

HCID 86732808HCID 86732808, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a yellow solution of 1-ethyl-5-fluoro-3-(hydroxymethyl)-6,7-bis((4-methoxybenzyl)oxy) quinolin-4(1H)-one (11 g, 22.29 mmol) in Dichloromethane (DCM) (100 mL) was added manganese dioxide (19.38 g, 223 mmol). The mixture was stirred at rt for 6.5 h. The mixture was then filtered through Celite and washed with DCM, the filtrate was concentrated to afford 1-ethyl-5-fluoro-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinoline-3-carbaldehyde (9.8 g, 19.94 mmol, 89% yield) as a yellow solid, which was used in the next step without further purification. LCMS: (M+H)+: 492.2.

Workup

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

Sources & evidence

ORD record
ord-ed085b47d1e144c79561dbd281ae20e5
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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