Acetic Acid → 3,4-dihydro-7-hydroxy-2-(3-pyridylmethyl)-1 (2H)-isoquinolinone

HRID 1609593Notes

Reaction equation

HRID 1609593 reaction equation
Br.C[O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][N:10]([CH2:15][C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)[C:11]2=[O:14])=[CH:6][CH:5]=1.[OH-].[Na+].C(O)(=O)C>C(OCC)(=O)C>[OH:3][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][N:10]([CH2:15][C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)[C:11]2=[O:14])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 543811613,4-dihydro-7-methoxy-2-(3-pyridylmethyl)-1 (2H)-isoquinolinone

Product 1

HCID 542355103,4-dihydro-7-hydroxy-2-(3-pyridylmethyl)-1 (2H)-isoquinolinoneYield 46.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 84 ml of 47% aqueous hydrogen bromide was added 11.3 g of 3,4-dihydro-7-methoxy-2-(3-pyridylmethyl)-1 (2H)-isoquinolinone, and the mixture was refluxed under heating for 4.5 hours. After ice cooling, the mixture was neutralized with aqueous sodium hydroxide, made weakly acidic with acetic acid and shaken with ethyl acetate. The organic layer was washed with water and saturated brine in order, dried over anhydrous magnesium sulfate and concentrated in vacuo. The resultant residue was chromatographed on a column of silica gel, eluting with ethyl acetate to give 5.00 g of the titled compound.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 4.5 hours
  3. washThe organic layer was washed with water and saturated brine in order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resultant residue was chromatographed on a column of silica gel
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-27c92c253f93437d9e5afd63078422b8
Source dataset
uspto-grants-1995_03
Patent number
US05401756

Reaction notes

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