2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 59703630, compound

HRID 556475Notes

Reaction equation

HRID 556475 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:14][C:13]2[C:8](=[CH:9][C:10](OC)=[CH:11][CH:12]=2)[N:7]1[C:17]1([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=2)[C:25]2[C:20](=[CH:21][C:22]([Cl:26])=[CH:23][CH:24]=2)[NH:19][C:18]1=[O:27])=[O:5])[CH3:2].C(C1C(=O)C([Cl:46])=C(Cl)C(=O)C=1C#N)#N>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[N:7]([C:17]2([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=3)[C:25]3[C:20](=[CH:21][C:22]([Cl:26])=[CH:23][CH:24]=3)[NH:19][C:18]2=[O:27])[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([Cl:46])[CH:9]=2)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 59703572HCID 59703572, compound

Product 1

HCID 59703630HCID 59703630, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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 ethyl ester (1.0 g, 1.9 mmol) and DDQ (0.73 g, 3.2 mmol) in toluene (50 mL) was heated to 90° C. for 4 h. Then the mixture was cooled to room temperature and washed with NaOH solution (10%) and water. The organic layer was dried with Na2SO4, concentrated in vacuo to give 0.9 g rac-6,6′-Dichloro-3′-(3-chloro-benzyl)-2′-oxo-2′,3′-dihydro-1′H-[1,3′]biindolyl-2-carboxylic acid ethyl ester as yellow solid. MS: [M+H]+=513

Workup

  1. washwashed with NaOH solution (10%) and water
  2. dry with materialThe organic layer was dried with Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4cf7edc6b8bc4609ae473e34b2d4fd99
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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