2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 19902832, compound

HRID 2372179Notes

Reaction equation

HRID 2372179 reaction equation
[O:1]=[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][CH:3]1[C:4]([O-])=O.ClC1C(=O)C(C#N)=C(C#N)C(=[O:19])C=1Cl.O1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>>[CH2:8]([C:9]1[NH:10][C:2](=[O:1])[CH:3]=[CH:4][C:30]=1[C:29]([O:28][CH2:27][CH3:26])=[O:19])[CH3:7]

Participants

4

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 312751,4-DioxaneHCID 78349156HCID 78349156, compound

Product 1

HCID 19902832HCID 19902832, compound

Procedure

A mixture of the above oxonicotinate (2.7 g, 13.7 mmol) and 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) in 100 ml of dioxane is heated to reflux overnight, after which the dioxane is removed by rotoevaporation The residue is dissolved in chloroform and extracted with sat. sodium bicarbonate. The organic fraction is washed with brine and dried and the solvent is removed. The resulting solid is triturated with small volumes of ether/hexane. The solid left undissolved is dried to give ethyl 1,6-dihydro-2-ethyl-6-oxonicotinate.

Workup

  1. temperatureis heated
  2. temperatureto reflux overnight
  3. customafter which the dioxane is removed by rotoevaporation The residue
  4. dissolutionis dissolved in chloroform
  5. extractionextracted with sat. sodium bicarbonate
  6. washThe organic fraction is washed with brine
  7. customdried
  8. customthe solvent is removed
  9. customThe resulting solid is triturated with small volumes of ether/hexane
  10. waitThe solid left undissolved
  11. customis dried

Sources & evidence

ORD record
ord-eccfacfa6eaa4d3ca79cf3b2605dd50f
Source dataset
uspto-grants-1992_03
Patent number
US05098462

Reaction notes

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