Cesium carbonate → HCID 66597019, compound

HRID 1811407Notes

Reaction equation

HRID 1811407 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][C:10](=[O:16])[NH:11]2.I[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.N[C@@H]1CCCC[C@H]1N.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.[Cu]I>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][C:10](=[O:16])[N:11]2[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 11575IodobenzeneHCID 438061,2-Diaminocyclohexane, trans-HCID 66596967HCID 66596967, compound

Product 1

HCID 66597019HCID 66597019, compoundYield 93.8%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Procedure

5-(1,3-Dioxolan-2-yl)-3,4-dihydro-1H-quinolin-2-one (2.30 g, 10.5 mmol), iodobenzene (3.5 ml, 31.5 mmol), copper(I) iodide (400 mg, 2.10 mmol), trans-1,2-diaminocyclohexane (0.129 ml, 1.05 mmol) and cesium carbonate (6.84 g, 21.0 mmol) were stirred in 30 ml of 1,4-dioxane under reflux for three days. After cooling, the insoluble matter was filtered off through a Celite pad. Ethyl acetate and water were added to the filtrate, and the resulting mixture was washed (twice with water and once with a saturated sodium chloride solution), dried (MgSO4), and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3→1:1) to thereby obtain 2.91 g (yield: 92%) of 5-(1,3-dioxolan-2-yl)-1-phenyl-3,4-dihydro-1H-quinolin-2-one as a white solid.

Workup

  1. temperatureunder reflux for three days
  2. temperatureAfter cooling
  3. filtrationthe insoluble matter was filtered off through a Celite pad
  4. additionEthyl acetate and water were added to the filtrate
  5. washthe resulting mixture was washed (twice with water
  6. dry with materialonce with a saturated sodium chloride solution), dried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3→1:1)

Sources & evidence

ORD record
ord-eb16ed164d9743ae959155248ca0640a
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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