HCID 86732798, compound → HCID 86732797, compound

HRID 525929Notes

Reaction equation

HRID 525929 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])=[N: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: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]([CH:34]=[O:35])=[N:6][N:7]2[CH2:32][CH3:33]

Participants

4

Reactant 1

HCID 86732798HCID 86732798, compound

Product 1

HCID 86732797HCID 86732797, compoundYield 56.7%

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)cinnolin-4(1H)-one (6 g, 8.45 mmol) in Dichloromethane (DCM) (100 mL) was added manganese dioxide (12.11 g, 118 mmol), and the mixture was stirred at r.t. overnight. Solid was filtered off and washed with DCM. The filtrate was concentrated to afford 5-chloro-1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydrocinnoline-3-carbaldehyde (4 g, 4.79 mmol, 56.7% yield) as a crude dark brown solid. LCMS: (M+H)+: 509.3.

Workup

  1. filtrationSolid was filtered off
  2. washwashed with DCM
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-9d031f27c5a643cb8093f33bd70875a1
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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