Sodium Hydroxide → 4-(3-acetyl-6-bromo-1-oxo-4-phenyl-1H-isoquinolin-2-ylmethyl)benzoic Acid

HRID 750315Notes

Reaction equation

HRID 750315 reaction equation
[C:1]([C:4]1[N:5]([CH2:22][C:23]2[CH:32]=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[CH:25][CH:24]=2)[C:6](=[O:21])[C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:11][C:10]([Br:20])=[CH:9][CH:8]=2)(=[O:3])[CH3:2].[OH-].[Na+]>CO.O1CCCC1>[C:1]([C:4]1[N:5]([CH2:22][C:23]2[CH:24]=[CH:25][C:26]([C:27]([OH:29])=[O:28])=[CH:31][CH:32]=2)[C:6](=[O:21])[C:7]2[C:12]([C:13]=1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[CH:11][C:10]([Br:20])=[CH:9][CH:8]=2)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69156099methyl 4-(3-acetyl-6-bromo-1-oxo-4-phenyl-1H-isoquinolin-2-ylmethyl)benzoate

Product 1

HCID 691563104-(3-acetyl-6-bromo-1-oxo-4-phenyl-1H-isoquinolin-2-ylmethyl)benzoic AcidYield 94.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 4-(3-acetyl-6-bromo-1-oxo-4-phenyl-1H-isoquinolin-2-ylmethyl)benzoate (510 mg) in methanol (5 ml) and tetrahydrofuran (5 ml) was added 1N aqueous sodium hydroxide solution (4 ml) and the mixture was stirred at room temperature for 12 hrs. The solvent was evaporated under reduced pressure and water was added. The mixture was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The extract was washed with saturated brine and dried by adding sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was recrystallized from methanol to give the title compound (467 mg, 94%).

Workup

  1. customThe solvent was evaporated under reduced pressure and water
  2. additionwas added
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. customdried
  6. additionby adding sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe obtained residue was recrystallized from methanol

Sources & evidence

ORD record
ord-2b5a1e024e374107b0f688d45a589d3d
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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