2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 68707430, compound

HRID 222096Notes

Reaction equation

HRID 222096 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:17]2[CH2:16][CH2:15][C:14]3[NH:13][N:12]=[CH:11][C:10]=3[C:9]=2[N:8]([CH3:18])[CH:7]=1)=[O:5])[CH3:2].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>O1CCOCC1>[CH2:1]([O:3][C:4]([C:6]1[C:17]2[C:9](=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][N:12]=[CH:11]3)[N:8]([CH3:18])[CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 68708273HCID 68708273, compound

Product 1

HCID 68707430HCID 68707430, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 1-methyl-1,4,5,6-tetrahydro-1,6,7-triaza-as-indacene-3-carboxylic acid ethyl ester A1 (1.65 mmol) in dioxane (45 mL) under argon, DDQ (1.2 eq) was added and the reaction was kept at 100° C. for 2 h. The residue obtained after solvent evaporation was taken up with AcOEt and the organic phase was washed with water, dried (Na2SO4) and concentrated to give a crude product that was purified using the Biotage Horizon system (AcOEt/hexane 2:8). The title product was obtained as a solid (30% yield). ESI (+) MS: m/z 244 (MH+). 1H NMR: 1.34 (t, 3H), 4.13 (s, 3H), 4.28 (q, 2H), 7.40 (d, 1H), 7.96 (s, 1H), 8.00 (d, 1H), 8.41 (s, 1H), 13.28 (bs, 1H).

Workup

  1. customThe residue obtained
  2. customafter solvent evaporation
  3. washthe organic phase was washed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customto give a crude product that
  7. customwas purified

Sources & evidence

ORD record
ord-93a58d9496474be8977ed23fcd8db02a
Source dataset
uspto-grants-2012_06
Patent number
US08207180B2

Reaction notes

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