2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 86680198, compound

HRID 2402351Notes

Reaction equation

HRID 2402351 reaction equation
COC1C=CC(C[N:8](CC2C=CC(OC)=CC=2)[C:9]2[CH:10]=[C:11]([C:16]([CH:21]([C:26]([O:28][CH3:29])=[O:27])[C:22]([O:24][CH3:25])=[O:23])([CH:18]3[CH2:20][CH2:19]3)[CH3:17])[CH:12]=[CH:13][C:14]=2[Cl:15])=CC=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.C(=O)(O)[O-].[Na+]>ClCCl.O>[NH2:8][C:9]1[CH:10]=[C:11]([C:16]([CH:21]([C:26]([O:28][CH3:29])=[O:27])[C:22]([O:24][CH3:25])=[O:23])([CH:18]2[CH2:19][CH2:20]2)[CH3:17])[CH:12]=[CH:13][C:14]=1[Cl:15]

Participants

6

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 516892Sodium BicarbonateHCID 70914952HCID 70914952, compound

Product 1

HCID 86680198HCID 86680198, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

627 mg (1.11 mmol) of dimethyl (1-{3-[bis(4-methoxybenzyl)amino]-4-chlorophenyl}-1-cyclo-propylethyl)malonate were taken up in 60 ml of dichloromethane and 15 ml of water. 553 mg (2.44 mmol) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) were then added, and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was then added to about 50 ml of saturated aqueous sodium bicarbonate solution. The phases were separated, and the aqueous phase was extracted three more times with in each case about 10 ml of dichloromethane. The combined organic phases were dried over magnesium sulphate and concentrated under reduced pressure. The product was isolated from the residue by preparative RP-HPLC (mobile phase methanol/water). This gave 283 mg of the target product (78% of theory).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted three more times with in each case about 10 ml of dichloromethane
  3. dry with materialThe combined organic phases were dried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe product was isolated from the residue by preparative RP-HPLC (mobile phase methanol/water)

Sources & evidence

ORD record
ord-46539b180661477983adaf335d495101
Source dataset
uspto-grants-2014_08
Patent number
US08796335B2

Reaction notes

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