2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1-Acetyl-1H-indole-5-carboxylic acid

HRID 1393675Notes

Reaction equation

HRID 1393675 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([OH:15])=[O:14])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([OH:15])=[O:14])=[CH:10][CH:11]=2)[CH:6]=[CH:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 52955471-acetylindoline-5-carboxylic acid

Product 1

HCID 230919251-Acetyl-1H-indole-5-carboxylic acidYield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

1-Acetyl-2,3-dihydro-1H-indole-5-carboxylic acid (100 mg) was suspended in 1,4-dioxane (3 ml), and 2,3-dichloro-5,6-dicyano-p-benzoquinone (445 mg) was added thereto and stirred for 16 hours at 110° C. Solids were removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by preparative thin-layer chromatography (developing solvent; dichloromethane:methanol 20:1) to give the title compound (98 mg, Y.:99%).

Workup

  1. customSolids were removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by preparative thin-layer chromatography (developing solvent; dichloromethane:methanol 20:1)

Sources & evidence

ORD record
ord-790cda9e7a7c423c8eb5e2d9510bb61d
Source dataset
uspto-grants-2008_03
Patent number
US07345180B2

Reaction notes

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