2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 59703629, compound

HRID 556489Notes

Reaction equation

HRID 556489 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[CH:31]=3)([N:12]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH2:14][CH:13]3[C:21]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[O:22])[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[CH:31]=3)([N:12]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:14]=[C:13]3[C:21]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[O:22])[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 59703623HCID 59703623, compound

Product 1

HCID 59703629HCID 59703629, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

At room temperature, 6′-Chloro-3′-(3-chloro-benzyl)-2-(morpholine-4-carbonyl)-2,3,1′,3′-tetrahydro-[1,3′]biindolyl-2′-one (60 mg, 0.115 mmol) and DDQ (47 mg, 0.207 mmol) were dissolved in 5 ml toluene. After stirred overnight, the solution was concentrated and then the residue was dissolved in EtOAc. The organic layer was washed with 10% NaOH aqueous solution and dried, concentrated to obtain crude product. The crude product was purified by chromatography to obtain 20 mg yellow solid rac-6′-Chloro-3′-(3-chloro-benzyl)-2-(morpholine-4-carbonyl)-1′,3′-dihydro-[1,3′]biindolyl-2′-one. MS: 520 (M+H)+.

Workup

  1. concentrationthe solution was concentrated
  2. dissolutionthe residue was dissolved in EtOAc
  3. washThe organic layer was washed with 10% NaOH aqueous solution
  4. customdried
  5. concentrationconcentrated
  6. customto obtain crude product
  7. customThe crude product was purified by chromatography

Sources & evidence

ORD record
ord-ad9e69ee7bc64dd8a75abd523ee4c913
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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