2-benzyl-6-bromo-3-(1-hydroxyethyl)-4-phenyl-2H-isoquinolin-1-one → 3-acetyl-2-benzyl-6-bromo-4-phenyl-2H-isoquinolin-1-one

HRID 750265Notes

Reaction equation

HRID 750265 reaction equation
[CH2:1]([N:8]1[C:17]([CH:18]([OH:20])[CH3:19])=[C:16]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Br:27])[CH:14]=2)[C:9]1=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1.[O-2].[Mn+4].[O-2]>[C:18]([C:17]1[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:9](=[O:28])[C:10]2[C:15]([C:16]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[CH:14][C:13]([Br:27])=[CH:12][CH:11]=2)(=[O:20])[CH3:19]

Participants

4

Reactant 1

HCID 230610042-benzyl-6-bromo-3-(1-hydroxyethyl)-4-phenyl-2H-isoquinolin-1-one

Product 1

HCID 230606723-acetyl-2-benzyl-6-bromo-4-phenyl-2H-isoquinolin-1-oneYield 60.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst4×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-benzyl-6-bromo-3-(1-hydroxyethyl)-4-phenyl-2H-isoquinolin-1-one (250 mg) in THF (5 ml) was added manganese(IV) oxide (500 mg), and the mixture was heated under reflux for 1 hr. To the reaction mixture was add manganese(IV) oxide (500 mg) and the mixture was heated under reflux for 1 hr, manganese(IV) oxide (500 mg) was added and the mixture was heated under reflux for 1 hr, and manganese(IV) oxide (500 mg) was added and the mixture was heated under reflux for 12 hrs. The reaction mixture was filtered and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography (hexane-hexane:ethyl acetate=8:1) and recrystallized (ethyl acetate-hexane) to give the title compound (150 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hr
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 1 hr
  5. temperaturethe mixture was heated
  6. temperatureunder reflux for 1 hr
  7. temperaturethe mixture was heated
  8. temperatureunder reflux for 12 hrs
  9. filtrationThe reaction mixture was filtered
  10. concentrationthe filtrate was concentrated
  11. customThe obtained residue was purified by silica gel column chromatography (hexane-hexane:ethyl acetate=8:1)
  12. customrecrystallized (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-d3ed62cbaa01469591e40e2ebb28bc3b
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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