1,4-Dioxane → 5-Nitro-2-(tetrahydro-pyran-4-ylmethyl)-2H-isoquinolin-1-one

HRID 1037771Notes

Reaction equation

HRID 1037771 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7]O[C:9]2=[O:14])([O-:3])=[O:2].[O:15]1[CH2:20][CH2:19][CH:18]([CH2:21][NH2:22])[CH2:17][CH2:16]1.O1CCOCC1>CCOC(C)=O>[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:22]([CH2:21][CH:18]1[CH2:19][CH2:20][O:15][CH2:16][CH2:17]1)[C:9]2=[O:14])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 27732104-AminomethyltetrahydropyranHCID 100127605-nitro-1H-isochromen-1-one

Product 1

HCID 595794195-Nitro-2-(tetrahydro-pyran-4-ylmethyl)-2H-isoquinolin-1-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5-Nitro-isochromen-1-one (1.0 g, 0.0052 mol) and C-(tetrahydro-pyran-4-yl)-methylamine (0.72 g, 0.0063 mol) were stirred in 1,4-dioxane (3 mL, 0.04 mol) at 120° C. for 18 hours. The mixture was diluted with EtOAc (200 mL), washed with 1 N HCl (30 mL×2), brine (30 mL) and dried over Na2SO4. After the filtration the solvent was removed and the residue was purified via flash chromatography (40 g of silica gel, 40% EtOAc/Hexanes) to give a yellow oil. MS m/z (M+H) 289.1.

Workup

  1. washwashed with 1 N HCl (30 mL×2), brine (30 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationAfter the filtration the solvent
  4. customwas removed
  5. customthe residue was purified via flash chromatography (40 g of silica gel, 40% EtOAc/Hexanes)
  6. customto give a yellow oil

Sources & evidence

ORD record
ord-a087e6ff07d544c1879274628650eb37
Source dataset
uspto-grants-2013_10
Patent number
US08546579B2

Reaction notes

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