Water → HCID 57486896, compound

HRID 15356Notes

Reaction equation

HRID 15356 reaction equation
[CH:1]([C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][NH:9][C:10]2=[O:13])=[CH:5][CH:4]=1)=[CH2:2].[H-].[Na+].I[CH3:17].O>C1(C)C=CC=CC=1.O1CCCC1>[CH:1]([C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][N:9]([CH3:17])[C:10]2=[O:13])=[CH:5][CH:4]=1)=[CH2:2]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodide2×HCID 24758Sodium hydrideHCID 574868957-Vinyl-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 57486896HCID 57486896, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-ethenyl-3,4-dihydro-1(2H)-isoquinolinone (224 mg, 1.295 mmol) in toluene (2 ml) and tetrahydrofuran (2 ml) at 0° C. was added sodium hydride (60% in oil, 37 mg, 1.554 mmol). The reaction mixture was warmed to room temperature and stirred for 0.5 h before addition of iodomethane (242 μl, 3.885 mmol). The reaction mixture was stirred at room temperature for 1 h before addition of additional iodomethane (242 μl, 3.885 mmol). The reaction mixture was then stirred at room temperature for a further 1 h before addition of water (20 ml). The mixture was extracted with 10% methanol/dichloromethane (3×100 ml), the organic layers were dried with magnesium sulphate and evaporated. Chromatography on silica, eluting with 0-100% ethyl acetate/hexane, gave the product (181 mg, 75%).

Workup

  1. extractionThe mixture was extracted with 10% methanol/dichloromethane (3×100 ml)
  2. dry with materialthe organic layers were dried with magnesium sulphate
  3. customevaporated
  4. washChromatography on silica, eluting with 0-100% ethyl acetate/hexane

Sources & evidence

ORD record
ord-ab1fa592bb99465b8b8a7b4b43aa06d2
Source dataset
uspto-grants-2010_06
Patent number
US07732461B2

Reaction notes

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