Methanol → HCID 69155568, compound

HRID 750153Notes

Reaction equation

HRID 750153 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:26][C:27]2[CH:35]=[CH:34][C:30]3[O:31][CH2:32][O:33][C:29]=3[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:35]=[CH:34][C:30]3[O:31][CH2:32][O:33][C:29]=3[CH:28]=2)[C:7](=[O:25])[C:8]2[C:13]([C:14]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=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 69156239HCID 69156239, compound

Product 1

HCID 69155568HCID 69155568, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(benzo[1,3]dioxol-5-ylmethyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3,6-dicarboxylic acid dimethyl ester (300 mg) in THF (3 ml) were added methanol (3 ml) and 8N-aqueous sodium hydroxide solution (0.16 ml) at room temperature, and the mixture was stirred for 12 hrs. The reaction mixture was concentrated under reduced pressure, and 1N-hydrochloric acid was added to the residue. The aqueous layer of the mixture was acidified, and 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 (230 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and 1N-hydrochloric acid
  2. additionwas added to the residue
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-37c9cc996a7b42859de954266a44cdd4
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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