Water → 4-Benzyl-3-hydroxy-3,4-dihydro-1-isoquinolinone

HRID 432672Notes

Reaction equation

HRID 432672 reaction equation
[BH4-].[Na+].C(=[C:10]1[CH:21]=[CH:20][C:13]2[CH2:14][C:15]([NH:17][C:18](=[O:19])[C:12]=2[CH2:11]1)=[O:16])C1C=CC=CC=1.O>CO>[CH2:18]([CH:14]1[C:13]2[C:12](=[CH:11][CH:10]=[CH:21][CH:20]=2)[C:18](=[O:19])[NH:17][CH:15]1[OH:16])[C:12]1[CH:13]=[CH:20][CH:21]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 1317242574-Benzylidenehomophthalimide

Product 1

HCID 187602464-Benzyl-3-hydroxy-3,4-dihydro-1-isoquinolinone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (1.2 g, 32 mmol) was added in portions to a stirred suspension of 4-benzylidenehomophthalimide (2 g, 8 mmol) in methanol (50 ml), then the stirred mixture was heated under reflux for 4 hours, cooled to ambient temperature and added to water (200 ml). The product was extracted into ethyl acetate (3×50 ml), the combined extracts were washed with water (2×30 ml), dried (MgSO4) and the solvent was removed in vacuo. The residue was dissolved in the minimum volume of ether and sufficient hexane was added to precipitate the product. The resulting solid was collected by filtration, washed with hexane (20 ml) and dried in vacuo to give the 4-benzyl-3-hydroxy-3,4-dihydro-1-isoquinolinone intermediate which was used without purification.

Workup

  1. temperaturethe stirred mixture was heated
  2. temperatureunder reflux for 4 hours
  3. extractionThe product was extracted into ethyl acetate (3×50 ml)
  4. washthe combined extracts were washed with water (2×30 ml)
  5. dry with materialdried (MgSO4)
  6. customthe solvent was removed in vacuo
  7. dissolutionThe residue was dissolved in the minimum volume of ether and sufficient hexane
  8. additionwas added
  9. customto precipitate the product
  10. filtrationThe resulting solid was collected by filtration
  11. washwashed with hexane (20 ml)
  12. customdried in vacuo

Sources & evidence

ORD record
ord-cbdc28dc43ce4b18b5de0d1999055ba9
Source dataset
uspto-grants-2003_12
Patent number
US06664269B2

Reaction notes

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