Acetic Anhydride → 6-(3-acetoxy-propoxy)-7-methoxy-1-(3-methoxy-benzyl)-1H-isoquinoline-2-carboxylic acid ethyl ester

HRID 1833167Notes

Reaction equation

HRID 1833167 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][C:10]([O:21][CH3:22])=[C:11]([O:16][CH2:17][CH2:18][CH2:19][OH:20])[CH:12]=2)[CH:7]1[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=1)=[O:5])[CH3:2].[C:32](OC(=O)C)(=[O:34])[CH3:33]>N1C=CC=CC=1>[CH2:1]([O:3][C:4]([N:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][C:10]([O:21][CH3:22])=[C:11]([O:16][CH2:17][CH2:18][CH2:19][O:20][C:32](=[O:34])[CH3:33])[CH:12]=2)[CH:7]1[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 69558143HCID 69558143, compound

Product 1

HCID 695582746-(3-acetoxy-propoxy)-7-methoxy-1-(3-methoxy-benzyl)-1H-isoquinoline-2-carboxylic acid ethyl esterYield 99%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 6-(3-hydroxy-propoxy)-7-methoxy-1-(3-methoxy-benzyl)-1H isoquinoline-2-carboxylic acid ethyl ester (130 mg, 0.30 mmol) in pyridine (2 μL) was added acetic anhydride (1 mL). The reaction mixture was stirred at room temperature for 15 hrs. The solvent was evaporated and toluene was added to remove pyridine completely. The crude product 6-(3-acetoxy-propoxy)-7-methoxy-1-(3-methoxy-benzyl)-1H-isoquinoline-2-carboxylic acid ethyl ester (142, 99% yield) was used without further purification.

Workup

  1. customThe solvent was evaporated
  2. additiontoluene was added
  3. customto remove pyridine completely

Sources & evidence

ORD record
ord-3da3b78c8c5c49318bf52d87048a0ad6
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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