Methanol → HCID 69156333, compound

HRID 750371Notes

Reaction equation

HRID 750371 reaction equation
C[O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[C:20]([C:21](=[O:23])[CH3:22])=[C:19]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([Cl:30])[CH:17]=3)[C:12]2=[O:31])=[CH:6][CH:5]=1.CO.[OH-].[Na+]>C1COCC1>[C:21]([C:20]1[N:11]([CH2:10][C:7]2[CH:6]=[CH:5][C:4]([C:3]([OH:32])=[O:2])=[CH:9][CH:8]=2)[C:12](=[O:31])[C:13]2[C:18]([C:19]=1[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[CH:17][C:16]([Cl:30])=[CH:15][CH:14]=2)(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 69157468HCID 69157468, compound

Product 1

HCID 69156333HCID 69156333, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[(3-acetyl-6-chloro-1-oxo-4-phenyl-1H-isoquinolin-2-yl)methyl]benzoic acid methyl ester (1.5 g) in THF (15 ml) were added methanol (15 ml) and 8N-aqueous sodium hydroxide solution (0.8 ml) at room temperature, and the mixture was stirred for 12 hrs. The reaction mixture was concentrated under reduced pressure, water and 10% hydrochloric acid were added to the residue. The aqueous layer was acidified and extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by recrystallization (ethyl acetate-hexane) to give the title compound (1.2 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, water and 10% hydrochloric acid
  2. additionwere 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. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by recrystallization (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-47d40199fd0b4ca4bcd3ae8e08abd15c
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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