2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 118557796, compound

HRID 2207183Notes

Reaction equation

HRID 2207183 reaction equation
[C:1]([C:4]1[CH:9]([CH2:10][CH:11]2[CH2:20][CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16](OC)[CH:17]=3)[C:12]2=[O:23])[CH:8]=[CH:7][N:6]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]([F:34])([F:33])[F:32])[CH:5]=1)(=[O:3])[CH3:2].C(C1C(=O)C([Cl:45])=C(Cl)[C:39](=[O:40])C=1C#N)#N>C(#N)C>[Cl-:45].[C:1]([C:4]1[CH:5]=[N+:6]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]([F:32])([F:34])[F:33])[CH:7]=[CH:8][C:9]=1[CH2:10][C:11]1([O:40][CH3:39])[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]1=[O:23])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 118557914HCID 118557914, compound

Product 1

HCID 118557796HCID 118557796, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of compound 67 (30.0 mg, 0.064 mmol) in acetonitrile (1 mL) was added DDQ (1 equiv) in one portion at room temperature. After completion of the reaction, acetonitrile was removed under reduced pressure and the residue was taken up in dichloromethane (10 mL). The organic layer was successively washed with aqueous solution of HCl 1M and brine, dried over magnesium sulfate, filtered and concentrated to dryness. The obtained solid was placed in presence of anion exchange resin (Amberlyst Cl−) in acetonitrile for 24 h. After filtration and concentration, the title compound 83 was obtained as a yellow solid (Yield 19.3 mg, 60%).

Workup

  1. customwas removed under reduced pressure
  2. washThe organic layer was successively washed with aqueous solution of HCl 1M and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-00b243696ea44d5b8657452c3559111b
Source dataset
uspto-grants-2016_06
Patent number
US09376387B2

Reaction notes

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