6-Butoxy-7-methoxy-1-(3-methoxy-benzyl)-1,2-dihydro-isoquinoline-4-carbaldehyde → 6-Butoxy-7-methoxy-1-(3-methoxy-benzyl)-isoquinoline-4-carbaldehyde

HRID 1833150Notes

Reaction equation

HRID 1833150 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH3:17])[CH:12]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=1)[NH:11][CH:10]=[C:9]2[CH:27]=[O:28])[CH2:2][CH2:3][CH3:4]>C(Cl)(Cl)Cl.[O-2].[Mn+4].[O-2]>[CH2:1]([O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH3:17])[C:12]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=1)=[N:11][CH:10]=[C:9]2[CH:27]=[O:28])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 220482446-Butoxy-7-methoxy-1-(3-methoxy-benzyl)-1,2-dihydro-isoquinoline-4-carbaldehyde

Product 1

HCID 220482946-Butoxy-7-methoxy-1-(3-methoxy-benzyl)-isoquinoline-4-carbaldehydeYield 99.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To a stirred solution of 6-butoxy-7-methoxy-1-(3-methoxy-benzyl)-1,2-dihydro-isoquinoline-4-carbaldehyde (200 mg, 0.53 mmol) in chloroform (6 mL) was added manganese (IV) oxide (536 mg, 5.34 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-butoxy-7-methoxy-1-(3-methoxy-benzyl)-isoquinoline-4-carbaldehyde (200 mg, 99% yield). The crude product was 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-3c570257739e4920be79cdda374406db
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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