2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 10236283, compound

HRID 1357063Notes

Reaction equation

HRID 1357063 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][C:14]([OH:20])=[CH:15][CH:16]=2)[O:11][CH:10]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.[O-]S([O-])=O.[Na+].[Na+]>O1CCOCC1>[OH:8][C:6]1[CH:5]=[CH:4][C:3]2[C:9]3[C:18](=[O:19])[C:17]4[CH:16]=[CH:15][C:14]([OH:20])=[CH:13][C:12]=4[O:11][C:10]=3[O:1][C:2]=2[CH:7]=1

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 24437Sodium SulfiteHCID 52805204H-1-Benzopyran-4-one, 3-(2,4-dihydroxyphenyl)-7-hydroxy-

Product 1

HCID 10236283HCID 10236283, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 15 (0.25 g, 0.93 mmol) and DDQ (0.42 g, 1.87 mmol) in dioxane was heated to 90° C. for 45 min. The reaction was allowed to cool and poured into 10% Na2SO3 and extracted with EtOAc. The EtOAc was dried over MgSO4, filtered and concentrated to give a yellow solid that was triturated with MeOH to give 16 as a white solid (0.050 g): Mp>300° C.; 1H NMR (DMSO d6) δ 10.88 (br s, 1H), 9.93 (br s, 1H), 8.05 (d, 1H, J=8.6 Hz), 7.77 (d, 1H, J=8.4 Hz), 7.10 (d, 1H, J=1.9 Hz), 7.05 (d, 1H, J=2.0 Hz), 7.01 (dd, 1H, J=8.6 Hz, 2.1 Hz), 6.92 (dd, 1H, J=8.4 Hz, 1.9 Hz); MS FI (neg) 267 (M−H)−.

Workup

  1. temperatureto cool
  2. extractionextracted with EtOAc
  3. dry with materialThe EtOAc was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a yellow solid
  7. customthat was triturated with MeOH

Sources & evidence

ORD record
ord-667700456cd841dcbcc2bf630c7edf94
Source dataset
uspto-grants-2003_07
Patent number
US06589980B2

Reaction notes

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