Potassium Hydroxide → HCID 22048278, compound

HRID 1833222Notes

Reaction equation

HRID 1833222 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:22][CH3:23])=[C:11]([O:18]C(=O)C)[CH:12]=2)[CH:7]1[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32][CH3:33])[CH:26]=1)=O)C.[OH-].[K+]>CO>[OH:18][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][C:10]=1[O:22][CH3:23])[CH:7]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32][CH3:33])[CH:26]=1)[NH:6][CH:15]=[C:14]2[CH:16]=[O:17]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 21034896HCID 21034896, compound

Product 1

HCID 22048278HCID 22048278, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-acetoxy-1-(3-ethoxy-benzyl)-4-formyl-7-methoxy-1H-isoquinoline-2-carboxylic acid ethyl ester (1.0 g, 2.20 mmol) in methanol (50 mL) was added powdered potassium hydroxide (741 mg, 11.1 mmol) at room temperature. The mixture was stirred at room temperature for 14 hrs. The solvent was evaporated and the residue was diluted with water (50 mL). The aqueous phase was extracted with ethyl acetate (2×50 mL). The combined extracts were washed with saturated aqueous sodium chloride solution (50 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to afford 6-hydroxy-7-methoxy-1-(3-ethoxy-benzyl)-1,2-dihydro-isoquinoline-4-carbaldehyde (660 mg, 88% yield). The crude product was used without further purification.

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was diluted with water (50 mL)
  3. extractionThe aqueous phase was extracted with ethyl acetate (2×50 mL)
  4. washThe combined extracts were washed with saturated aqueous sodium chloride solution (50 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-22ae1ef71e4946679f96b10f36793c61
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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