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

HRID 1833149Notes

Reaction equation

HRID 1833149 reaction equation
C(OC([N:6]1[CH:15]=[C:14]([CH:16]=[O:17])[C:13]2[C:8](=[CH:9][C:10]([O:23][CH3:24])=[C:11]([O:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:12]=2)[CH:7]1[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH3:33])[CH:27]=1)=O)C.[OH-].[K+]>CO>[CH2:19]([O:18][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][C:10]=1[O:23][CH3:24])[CH:7]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH3:33])[CH:27]=1)[NH:6][CH:15]=[C:14]2[CH:16]=[O:17])[CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 865956376-butoxy-4-formyl-7-methoxy-1-(3-methoxy-benzyl)-1H-isoquinoline-2-carboxylic acid ethyl ester

Product 1

HCID 220482446-Butoxy-7-methoxy-1-(3-methoxy-benzyl)-1,2-dihydro-isoquinoline-4-carbaldehydeYield 87.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 6-butoxy-4-formyl-7-methoxy-1-(3-methoxy-benzyl)-1H-isoquinoline-2-carboxylic acid ethyl ester (286 mg, 0.60 mmol) in methanol (12 mL) was added powdered potassium hydroxide (341 mg, 6.08 mmol). The reaction mixture was stirred at room temperature for 15 hrs. The solvent was evaporated and the residue was diluted with ethyl acetate (20 mL) and water (20 mL). The aqueous phase was extracted with ethyl acetate (3×20 mL). The combined extracts were washed with saturated aqueous sodium chloride solution (20 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to afford 6-butoxy-7-methoxy-1-(3-methoxy-benzyl)-1,2-dihydro-isoquinoline-4-carbaldehyde (200 mg, 87% yield) as a yellow oil. The crude product was used without further purification.

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was diluted with ethyl acetate (20 mL) and water (20 mL)
  3. extractionThe aqueous phase was extracted with ethyl acetate (3×20 mL)
  4. washThe combined extracts were washed with saturated aqueous sodium chloride solution (20 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e6b52869ffb5473c8e439ff7af742735
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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