Sodium ethoxide → HCID 59497119, compound

HRID 2046520Notes

Reaction equation

HRID 2046520 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].Cl[C:6]1[C:19]2[C:10](=[C:11]3[C:16](=[CH:17][CH:18]=2)[CH:15]=[CH:14][CH:13]=[N:12]3)[N:9]=[C:8]([CH3:20])[CH:7]=1>C(O)C>[CH3:20][C:8]1[CH:7]=[C:6]([O:1][CH2:2][CH3:3])[C:19]2[C:10](=[C:11]3[C:16](=[CH:17][CH:18]=2)[CH:15]=[CH:14][CH:13]=[N:12]3)[N:9]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 59497129HCID 59497129, compound

Product 1

HCID 59497119HCID 59497119, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Solid sodium ethoxide (2.97 g, 48.0 mmol) was added to a 100 mL round-bottomed flask containing a solution of 4-chloro-2-methyl-[1,10]phenanthroline (1.10 g, 4.8 mmol) in ethanol (50 mL). The reaction mixture was refluxed for 18 hours. The solvent was removed in a rotary evaporator and the residue was treated with methylene choride (100 mL) and saturated NaHCO3 (100 mL) and transferred to a separatory funnel. The organic layer was washed with brine (100 mL), dried (Na2SO4), filtered and concentrated in vacuo. The solid residue was treated with ethyl ether, filtered, and dried yielding 0.89 g of a brown solid (78%).

Workup

  1. temperatureThe reaction mixture was refluxed for 18 hours
  2. customThe solvent was removed in a rotary evaporator
  3. additionthe residue was treated with methylene choride (100 mL) and saturated NaHCO3 (100 mL)
  4. customtransferred to a separatory funnel
  5. washThe organic layer was washed with brine (100 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. additionThe solid residue was treated with ethyl ether
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-d344f91da60f4cebbd2b730e0019affb
Source dataset
uspto-grants-2013_11
Patent number
US08592446B2

Reaction notes

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