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

HRID 1833160Notes

Reaction equation

HRID 1833160 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][C:16]=2[O:17][CH3:18])[CH:13]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=2)[NH:12][CH:11]=[C:10]3[CH:28]=[O:29])[CH2:5][CH2:4][CH2:3][CH2:2]1>C(Cl)(Cl)Cl.[O-2].[Mn+4].[O-2]>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][C:16]=2[O:17][CH3:18])[C:13]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=2)=[N:12][CH:11]=[C:10]3[CH:28]=[O:29])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 220484396-Cyclopentyloxy-7-methoxy-1-(3-methoxy-benzyl)-1,2-dihydro-isoquinoline-4-carbaldehyde

Product 1

HCID 220484086-Cyclopentyloxy-7-methoxy-1-(3-methoxy-benzyl)-isoquinoline-4-carbaldehydeYield 100.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To a stirred solution of 6-cyclopentyloxy-7-methoxy-1-(3-methoxy-benzyl)-1,2-dihydro-isoquinoline-4-carbaldehyde (280 mg, 0.71 mmol) in chloroform (8 mL) was addend manganese (IV) oxide (728 mg, 7.12 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-cyclopentyloxy-7-methoxy-1-(3-methoxy-benzyl)-isoquinoline-4-carbaldehyde (280 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-495b60aabc984b9ebe38fdc0fc0c51ff
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

Loading…