HCID 22048278, compound → HCID 135714882, compound

HRID 1833223Notes

Reaction equation

HRID 1833223 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 mL) 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 celite® 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 celite® pad
  2. washwashed with chloroform
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-365c2e2febcd4615befdad2834334287
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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