HCID 86732758, compound → HCID 86732759, compound

HRID 525893Notes

Reaction equation

HRID 525893 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)=[C:10]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[C:11]=2[F:13])[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](=[CH:8][C:9]([O:24][CH2:25][C:26]3[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=3)=[C:10]([O:14][CH2:15][C:16]3[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=3)[C:11]=2[F:13])[C:6](=[O:34])[C:5]([CH:35]=[O:36])=[CH:4]1)[CH3:2]

Participants

4

Reactant 1

HCID 86732758HCID 86732758, compound

Product 1

HCID 86732759HCID 86732759, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a yellow solution of 1-ethyl-8-fluoro-3-(hydroxymethyl)-6,7-bis((4-methoxybenzyl)oxy)quinolin-4(1H)-one (10 g, 20.26 mmol) in Dichloromethane (DCM) (100 mL) was added manganese dioxide (17.62 g, 203 mmol), and the mixture was stirred at 25° C. for 6.5 h. LCMS indicated completion of the reaction. The solid was filtered off through Celite and washed with DCM, the filtrate was concentrated to afford 1-ethyl-8-fluoro-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinoline-3-carbaldehyde (6.5 g, 13.22 mmol, 65.3% yield) as a yellow solid that was used in the next step without further purification. LCMS (M+H)+: 492.2.

Workup

  1. customcompletion of the reaction
  2. filtrationThe solid was filtered off through Celite
  3. washwashed with DCM
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9c77bd24071942c89d1c3dd431478b72
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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