2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 86680197, compound

HRID 2402347Notes

Reaction equation

HRID 2402347 reaction equation
COC1C=CC(C[N:8](CC2C=CC(OC)=CC=2)[C:9]2[CH:10]=[C:11]([CH:16]([C:25]3([CH3:28])[CH2:27][CH2:26]3)[CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[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]([CH:16]([C:25]2([CH3:28])[CH2:26][CH2:27]2)[CH2:17][C:18]([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:19])[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 70873216HCID 70873216, compound

Product 1

HCID 86680197HCID 86680197, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

159 mg (0.29 mmol) of tert-butyl 3-{3-[bis(4-methoxybenzyl)amino]-4-chlorophenyl}-3-(1-methylcyclopropyl)propanoate were taken up in 7 ml of dichloromethane and 1.2 ml of water. 145 mg (0.64 mmol) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) were then added, and the reaction solution was stirred at room temperature for 2 h. The reaction mixture was then added to 10 ml of saturated aqueous sodium bicarbonate solution. The phases were separated, and the aqueous phase was then 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 31 mg of the target product (34% of theory).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was then 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-c4dc6b14696e4ad59a842c27ef2d7b80
Source dataset
uspto-grants-2014_08
Patent number
US08796335B2

Reaction notes

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