2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 59703565, compound

HRID 556495Notes

Reaction equation

HRID 556495 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][C:9]([O:14][CH3:15])=[CH:10][CH:11]=2)[N:6]1[C:16]1([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=2)[C:24]2[C:19](=[CH:20][C:21]([Cl:25])=[CH:22][CH:23]=2)[NH:18][C:17]1=[O:26])=[O:4].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[N:6]([C:16]2([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=3)[C:24]3[C:19](=[CH:20][C:21]([Cl:25])=[CH:22][CH:23]=3)[NH:18][C:17]2=[O:26])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([O:14][CH3:15])[CH:8]=2)=[O:4]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 66992271Rac-6'-chloro-3'-(3-chloro-benzyl)-6-methoxy-2'-oxo-2,3,2',3'-tetrahydro-1'h-[1,3']biindolyl-2-carboxylic acid methyl ester

Product 1

HCID 59703565HCID 59703565, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To the solution of rac-6′-Chloro-3′-(3-chloro-benzyl)-6-methoxy-2′-oxo-2,3,2′,3′-tetrahydro-1′H-[1,3′]biindolyl-2-carboxylic acid methyl ester (0.65 g, 1.31 mmol) in 10 mL toluene was added DDQ (0.51 g, 2.23 mmol). The reaction mixture was stirred at room temperature for 6 hour. And the mixture was washed with water (3×10 mL). The organic solution was dried with Na2SO4 and concentrated in vacuo. The residue was purified with chromatography to give white solid. MS: 495 (M+H)+.

Workup

  1. washAnd the mixture was washed with water (3×10 mL)
  2. dry with materialThe organic solution was dried with Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified with chromatography
  5. customto give white solid

Sources & evidence

ORD record
ord-b4b4a96db1ee47359c4b3c33afd1f580
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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