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

HRID 1609592Notes

Reaction equation

HRID 1609592 reaction equation
[H-].[Na+].Cl.Cl[CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1.[CH3:12][O:13][C:14]1[CH:23]=[C:22]2[C:17]([CH2:18][CH2:19][NH:20][C:21]2=[O:24])=[CH:16][CH:15]=1.O>CN(C)C=O.C1(C)C=CC=CC=1>[CH3:12][O:13][C:14]1[CH:23]=[C:22]2[C:17]([CH2:18][CH2:19][N:20]([CH2:5][C:6]3[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=3)[C:21]2=[O:24])=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 24758Sodium hydrideHCID 135216727-Methoxy-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 543811613,4-dihydro-7-methoxy-2-(3-pyridylmethyl)-1 (2H)-isoquinolinoneYield 72.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 3.70 g of sodium hydride (about 60%) in 80 ml of dimethylformamide was added portionwise 5.30 g of 3-chloromethylpyridine hydrochloride under ice cooling. The mixture was stirred under ice cooling for 15 minutes, and a solution of 4.09 g of 3,4-dihydro-7-methoxy-1 (2H)-isoquinolinone in 30 ml of dimethylformamide was added dropwise in 15 minutes thereto. The mixture was stirred at 10° C. for 1 hour, mixed with water and shaken with toluene. The organic layer was washed with water, 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 4.50 g of the titled compound.

Workup

  1. stirringThe mixture was stirred at 10° C. for 1 hour
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was chromatographed on a column of silica gel
  6. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-22f35460b4f6485b8f0d23f5c0f3a0d7
Source dataset
uspto-grants-1995_03
Patent number
US05401756

Reaction notes

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