2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 15590980, compound

HRID 255634Notes

Reaction equation

HRID 255634 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:17][C:16](=[O:18])[C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][N:9]2[C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[CH:4][CH:3]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([C:19]3[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=3)[CH:10]=[C:11]([C:16](=[O:18])[CH:17]=2)[C:12]([O:14][CH3:15])=[O:13])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 14010717HCID 14010717, compound

Product 1

HCID 15590980HCID 15590980, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

In 20 ml of benzene was dissolved 1.0 g of methyl 6-(4-chlorophenyl)-1-(4-fluorophenyl)-4-oxo-1,4,5,6-tetrahydronicotinate, and to the resulting solution was added a mixed solution of 0.7 g of 2,3-dichloro-5,6-dicyano-p-benzoquinone and 5 ml of benzene at 80° C., after which they were reacted at the same temperature for 30 minutes. After completion of the reaction, the solvent was removed from the reaction mixture by distillation under reduced pressure, and the residue was suspended in 30 ml of chloroform and 30 ml of water This suspension was adjusted to a pH of 7.5 with sodium hydrogencarbonate, and the organic layer was then separated and washed successively with 30 ml of water and 30 ml of a saturated aqueous solution of sodium chloride, and then dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to obtain 0.85 g of methyl 6-(4-chlorophenyl)-1-(4-fluorophenyl)-4-oxo-1,4-dihydronicotinate having a melting point of 250°-254° C.

Workup

  1. customafter which they were reacted at the same temperature for 30 minutes
  2. customAfter completion of the reaction
  3. customthe solvent was removed from the reaction mixture by distillation under reduced pressure
  4. customthe organic layer was then separated
  5. washwashed successively with 30 ml of water and 30 ml of a saturated aqueous solution of sodium chloride
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-19f8df8cd7474938ae7dff1d601b125f
Source dataset
uspto-grants-1987_10
Patent number
US04698352

Reaction notes

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