Methanol → 2-Benzyl-3-(methoxycarbonyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-6-carboxylic acid

HRID 750173Notes

Reaction equation

HRID 750173 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:7](=[O:25])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([C:21]([O:23]C)=[O:22])=[CH:10][CH:9]=2)=[O:4].CO.[OH-].[Na+]>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:7](=[O:25])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([C:21]([OH:23])=[O:22])=[CH:10][CH:9]=2)=[O:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 691557242-benzyl-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3,6-dicarboxylic Acid Dimethyl Ester

Product 1

HCID 444517952-Benzyl-3-(methoxycarbonyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-6-carboxylic acidYield 98.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-benzyl-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3,6-dicarboxylic acid dimethyl ester (1.75 g) in THF (10 ml) were added methanol (10 ml) and 8N-aqueous sodium hydroxide solution (1 ml) at room temperature, and the mixture was stirred for 12 hrs. The reaction mixture was concentrated under reduced pressure and water was added, after which conc. hydrochloric acid (1 ml) was added. The mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was crystallized from ethyl acetate-hexane to give the title compound (1.67 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and water
  2. additionwas added
  3. additionafter which conc. hydrochloric acid (1 ml) was added
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-eaa67b392da540dda4c10e9c9b795438
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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