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Ethyl Acetate → 6-Benzyloxy-7-methoxy-1-(3-methoxy-benzyl)-isoquinoline-4-carbaldehyde

HRID 1833140
Notes
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Reaction equation

HRID 1833140 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:26][CH3:27])=[C:11]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:12]=2)[CH:7]1[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[CH:30]=1)=O)C.[OH-].[K+].C(OCC)(=O)C.CCCCCC.C(OCC)(=O)C>CO>[CH2:19]([O:18][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][C:10]=1[O:26][CH3:27])[C:7]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[CH:30]=1)=[N:6][CH:15]=[C:14]2[CH:16]=[O:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 210349396-benzyloxy-4-formyl-7-methoxy-1-(3-methoxy-benzyl)-1H-isoquinoline-2-carboxylic acid ethyl esterHCID 21226206Ethyl acetate hexane2×

Product 1

HCID 220483476-Benzyloxy-7-methoxy-1-(3-methoxy-benzyl)-isoquinoline-4-carbaldehydeYield 42.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-benzyloxy-4-formyl-7-methoxy-1-(3-methoxy-benzyl)-1H-isoquinoline-2-carboxylic acid ethyl ester (85 mg, 0.17 mmol) in methanol (3 mL) was added powdered potassium hydroxide (97.7 mg, 1.75 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 (20 mL). The aqueous phase was extracted with ethyl acetate (2×20 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 a crude oil. Flash chromatography (Merck Silica gel 60, 70–230 mesh, 50% ethyl acetate/hexane, 75% ethyl acetate/hexane, ethyl acetate) afforded 6-benzyloxy-7-methoxy-1-(3-methoxy-benzyl)-isoquinoline-4-carbaldehyde as a colorless oil (30 mg, 42% yield).

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was diluted with water (20 mL)
  3. extractionThe aqueous phase was extracted with ethyl acetate (2×20 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
  8. customto afford a crude oil

Sources & evidence

ORD record
ord-1318553e3d4d48c88fbd3c4d4f595619
Source dataset
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07067529B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes