Water → 7-(2-chlorobenzyloxy)-3,4-dihydro-2-(3-pyridylmethyl)-1 (2H)-isoquinolinone

HRID 1464302Notes

Reaction equation

HRID 1464302 reaction equation
[H-].[Na+].[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.Cl[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[Cl:30].O>CN(C)C=O.C(OCC)(=O)C>[Cl:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[CH2:23][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

Participants

7

Reactant 4

HCID 962WaterHCID 119062-Chlorobenzyl chlorideHCID 24758Sodium hydrideHCID 542355103,4-dihydro-7-hydroxy-2-(3-pyridylmethyl)-1 (2H)-isoquinolinone

Product 1

HCID 540122637-(2-chlorobenzyloxy)-3,4-dihydro-2-(3-pyridylmethyl)-1 (2H)-isoquinolinoneYield 96.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 32 mg of sodium hydride (about 60%) in 10 ml of dimethylformamide was added 100 mg of 3,4-dihydro-7-hydroxy-2-(3-pyridylmethyl)-1 (2H)-isoquinolinone, and the resultant mixture was stirred for 15 minutes. Then, 95 mg of 2-chloromethylchlorobenzene was added to the mixture, which was stirred at room temperature for 20 hours. After finishing the reaction, the mixture was mixed with water and shaken with ethyl acetate. The organic layer was 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 144 mg of the titled compound.

Workup

  1. customthe reaction
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe resultant residue was chromatographed on a column of silica gel
  5. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-a38e8921db0a4d739b100b2b687cba2b
Source dataset
uspto-grants-1994_04
Patent number
US05304556

Reaction notes

Loading…