Water → HCID 59961793, compound

HRID 2207151Notes

Reaction equation

HRID 2207151 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[NH:10][CH2:9][CH2:8]2.[CH2:16](I)[CH:17]=[CH2:18].O>CN(C=O)C.CCOC(C)=O>[CH2:18]([N:10]1[CH2:9][CH2:8][C:7]2[C:12](=[CH:13][CH:14]=[C:5]([O:4][CH3:3])[CH:6]=2)[C:11]1=[O:15])[CH:17]=[CH2:16]

Participants

7

Reactant 4

HCID 962WaterHCID 11166Allyl iodideHCID 24758Sodium hydrideHCID 106073926-methoxy-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 59961793HCID 59961793, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 95% NaH (1.2 equiv) in anhydrous DMF (2 mL) was slowly added a solution of amide 42 (198 mg, 1.12 mmol) at room temperature. The mixture was stirred at room temperature for 0.5 h after which time allyl iodide (1.2 equiv) was added. The resulting mixture was stirred for 4 hours at this temperature. After addition of water and extraction with EtOAc (3×), the resulting combined organic layers were dried over magnesium sulfate, filtered and concentrated to dryness. The residue was purified by column chromatography on SiO2 (Petroleum ether/EtOAc=1:1) to afford the title compound 43 as a white solid (Yield 242.3 mg, 99%).

Workup

  1. additionwas added
  2. dry with materialwere dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe residue was purified by column chromatography on SiO2 (Petroleum ether/EtOAc=1:1)

Sources & evidence

ORD record
ord-996929b9ce644a419953bb98d508b424
Source dataset
uspto-grants-2016_06
Patent number
US09376387B2

Reaction notes

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