2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 11099874, compound

HRID 377537Notes

Reaction equation

HRID 377537 reaction equation
[CH2:1]([O:3][C:4]([NH:6][N:7]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)=[CH:11][CH:10]([CH3:23])[CH2:9][C:8]1=[O:24])=[O:5])[CH3:2].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([NH:6][N:7]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:20])([F:21])[F:22])[CH:14]=2)=[CH:11][C:10]([CH3:23])=[CH:9][C:8]1=[O:24])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 10991490HCID 10991490, compound

Product 1

HCID 11099874HCID 11099874, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2.6 g (8 mmol) of 1-(ethoxycarbonyl)amino-3,4-dihydro-4-methyl-6-(3'-trifluoromethylphenyl)-2-(1H)-pyridone in 75 ml of toluene is treated with 2.3 g (10 mmol) of DDQ and the mixture is refluxed for 6 hours. After cooling, the reaction solution is filtered off by suction through Alox n and the filtrated is evaporated on a rotary evaporator. The oil which remains is purified by column chromatography on Alox n (eluent: ethyl acetate:methanol=95:5).

Workup

  1. temperaturethe mixture is refluxed for 6 hours
  2. temperatureAfter cooling
  3. filtrationthe reaction solution is filtered off by suction through Alox n
  4. customthe filtrated is evaporated on a rotary evaporator
  5. customThe oil which remains is purified by column chromatography on Alox n (eluent: ethyl acetate:methanol=95:5)

Sources & evidence

ORD record
ord-a071a562eac24012a5046d00ebd4c3ff
Source dataset
uspto-grants-2000_02
Patent number
US06028033

Reaction notes

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