2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 68705098, compound

HRID 222103Notes

Reaction equation

HRID 222103 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:17])[C:7]2[C:8]3[CH:9]=[N:10][NH:11][C:12]=3[CH2:13][CH2:14][C:15]=2[CH:16]=1)=[O:4].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:17])[C:7]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[C:12]1[C:8]=2[CH:9]=[N:10][NH:11]1)=[O:4]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 68706147HCID 68706147, compound

Product 1

HCID 68705098HCID 68705098, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1-methyl-1,4,5,6-tetrahydro-1,6,7-triaza-as-indacene-2-carboxylic acid methyl ester A2 (1.03 mmol) and DDQ (1 eq) in dry dioxane (15 mL) was refluxed for 1.5 h with stirring. After solvent removal the slurry was treated with water under vigorous stirring. The precipitate was filtered, washed with water and dried. Obtained the title compound (67%). ESI (+) MS: m/z 230 (MH+). 1H NMR (300 MHz): 3.89 (s, 3H), 4.34 (s, 3H), 7.17 (d, J=8.71, 1H), 7.26 (s, 1H), 7.28 (d, J=8.71, 1H), 8.38 (s, 1H), 13.32 (s, 1H).

Workup

  1. temperaturewas refluxed for 1.5 h
  2. customAfter solvent removal the slurry
  3. additionwas treated with water under vigorous stirring
  4. filtrationThe precipitate was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-e2dc3598769d4d60aee7fc4ee1ce4bef
Source dataset
uspto-grants-2012_06
Patent number
US08207180B2

Reaction notes

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