2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 20079377, compound

HRID 1654076Notes

Reaction equation

HRID 1654076 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]1[CH2:13][N:14]([CH2:17][C:18]([NH:20][CH:21]([CH:28]([CH3:30])[CH3:29])[C:22](=[O:27])[C:23]([F:26])([F:25])[F:24])=[O:19])[CH2:15][CH2:16][C:9]2=1)([OH:3])=[O:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.C(OCC)(=O)C>O1CCOCC1>[C:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]1[CH2:13][N:14]([CH2:17][C:18]([NH:20][CH:21]([CH:28]([CH3:30])[CH3:29])[C:22](=[O:27])[C:23]([F:25])([F:24])[F:26])=[O:19])[CH:15]=[CH:16][C:9]2=1)([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 8857Ethyl AcetateHCID 20079370HCID 20079370, compound

Product 1

HCID 20079377HCID 20079377, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-(8-Carboxy-1,2,3,4-tetrahydropyrido[3,4-b]indol-2-yl)-N-(3,3,3-trifluoro-1-isopropyl-2-oxopropyl)acetamide (0.14 g) was dissolved in dioxane (50 mL), and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (0.45 g) was added. The resulting solution was allowed to stir overnight. Ethyl acetate (150 mL) was added and the solution was washed (H2O, brine), dried, and evaporated. The resulting solid was recrystallized from ethyl acetate to give the title compound (0.056 g); mp 260-262° C.

Workup

  1. washthe solution was washed (H2O, brine)
  2. customdried
  3. customevaporated
  4. customThe resulting solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-995b4a82b7b54020acf12542629183a6
Source dataset
uspto-grants-1995_04
Patent number
US05405852

Reaction notes

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