HCID 22048278, compound → HCID 135714882, compound

HRID 1833233Notes

Reaction equation

HRID 1833233 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH:8]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][CH3:23])[CH:16]=1)[NH:7][CH:6]=[C:5]2[CH:24]=[O:25]>C(Cl)(Cl)Cl.[O-2].[Mn+4].[O-2]>[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][CH3:23])[CH:16]=1)=[N:7][CH:6]=[C:5]2[CH:24]=[O:25]

Participants

4

Reactant 1

HCID 22048278HCID 22048278, compound

Product 1

HCID 135714882HCID 135714882, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To a stirred solution of 6-hydroxy-7-methoxy-1-(3-ethoxy-benzyl)-1,2-dihydro-isoquinoline-4-carbaldehyde (660 mg, 1.95 mmol) in chloroform (30 μL) was addend manganese (IV) oxide (1.99 mg, 19.5 mmol). The reaction mixture was stirred at room temperature for 15 hrs, filtered through a celites pad, and washed with chloroform. The filtrate was concentrated in vacuo to afford 6-hydroxy-7-methoxy-1-(3-ethoxy-benzyl)-isoquinoline-4-carbaldehyde (600 mg, 89% yield). The crude product was used without further purification.

Workup

  1. filtrationfiltered through a celites pad
  2. washwashed with chloroform
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-1de5bcf8effb40d9a8844fd7f9407eff
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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