HCID 22048326, compound → HCID 22048336, compound

HRID 1833183Notes

Reaction equation

HRID 1833183 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[CH:15]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH2:29][CH3:30])[CH:23]=1)[NH:14][CH:13]=[C:12]2[CH:31]=[O:32])(=[O:3])[CH3:2]>C(Cl)(Cl)Cl.[O-2].[Mn+4].[O-2]>[C:1]([O:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[C:15]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH2:29][CH3:30])[CH:23]=1)=[N:14][CH:13]=[C:12]2[CH:31]=[O:32])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 22048326HCID 22048326, compound

Product 1

HCID 22048336HCID 22048336, compoundYield 101.6%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To a stirred solution of 6-(3-acetoxy-propoxy)-7-methoxy-1-(3-ethoxy-benzyl)-1,2-dihydro-isoquinoline-4-carbaldehyde (120 mg, 0.27 mmol) in chloroform (3 mL) was addend manganese (IV) oxide (279 mg, 2.7 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-(3-acetoxy-propoxy)-7-methoxy-1-(3-ethoxy-benzyl)-isoquinoline-4-carbaldehyde (120 mg, 99% 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-4b17579e03a44816a7b8422b06b0b09f
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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