2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 22997273, compound

HRID 1166052Notes

Reaction equation

HRID 1166052 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH2:5][N:6]1[C:14]2[C:9](=[C:10]([CH2:15][OH:16])[CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:17]([O:19][CH2:20][CH3:21])=[O:18].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[CH:15]([C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[CH:8]=[C:7]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:6]2[CH2:5][C:4]1[CH:22]=[CH:23][C:24]([Cl:25])=[C:2]([Cl:1])[CH:3]=1)=[O:16]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 22997275HCID 22997275, compound

Product 1

HCID 22997273HCID 22997273, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Ethyl N-(3,4-dichlorobenzyl)-4-hydroxymethylindole-2-carboxylate (5.17 g) and 2,3-dichloro-5,6-dicyanobenzoquinone (3.10 g) were stirred in dioxane (100 ml) at ambient temperature, overnight. The reaction mixture was concentrated in vacuo and the residue dissolved in dichloromethane (100 ml) and filtered. The filtrate was concentrated in vacuo and the residue purified by column chromatography using 10% ethyl acetate:iso-hexane as eluent to give product as a yellow solid (4.88 g, 95%); NMR δ(CD3SOCD3) 1.30 (t, 3H), 4.30 (q, 2H), 5.90 (s, 2H), 6.85 (m, 1H), 7.90 (m, 1H), 8.00 (m, 1H), 10.22 (s, 1H); M/z (+) 376.3 (MH+).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue dissolved in dichloromethane (100 ml)
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-6d1ebd17bbf2461dbac9a81c153d31c7
Source dataset
uspto-grants-2003_09
Patent number
US06613760B1

Reaction notes

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