2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 6-(4-(4-(2-Ethoxyphenyl)-1-piperazinyl)-1-butenyl)carbostyril

HRID 1285460Notes

Reaction equation

HRID 1285460 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH:18]=[CH:19][C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[NH:26][C:25](=[O:30])[CH2:24][CH2:23]3)[CH2:12][CH2:11]1)[CH3:2].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1C=CC=CC=1>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH:18]=[CH:19][C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[NH:26][C:25](=[O:30])[CH:24]=[CH:23]3)[CH2:12][CH2:11]1)[CH3:2]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 30670876-(4-(4-(2-Ethoxyphenyl)-1-piperazinyl)-1-butenyl)-3,4-dihydro-2(1H)-quinolinone

Product 1

HCID 30671076-(4-(4-(2-Ethoxyphenyl)-1-piperazinyl)-1-butenyl)carbostyril

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2.0 Grams of 6-{4-[4-(2-ethoxyphenyl)-1-piperazinyl]-1-butenyl}-3,4-dihydrocarbostyril and 3.5 g of DDQ were mixed in 20 ml of benzene and the mixture was refluxed by heating for 5 hours. The reaction mixture was then concentrated under a reduced pressure and the residue thus obtained was extracted with chloroform. The chloroform layer was washed with 5%-NaHCO3 aqueous solution three times then washed with water twice and dried. Chloroform was removed by distillation and the residue obtained was purified by a silica-gel column chromatography and recrystallized from methanol to obtain 0.12 g of 6-{4-[4-(2-ethoxyphenyl)-1-piperazinyl]-1-butenyl}carbostyril in colorless needle-like crystals. Melting point: 225°-228° C.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureby heating for 5 hours
  3. concentrationThe reaction mixture was then concentrated under a reduced pressure
  4. customthe residue thus obtained
  5. extractionwas extracted with chloroform
  6. washThe chloroform layer was washed with 5%-NaHCO3 aqueous solution three times
  7. washthen washed with water twice
  8. customdried
  9. customChloroform was removed by distillation
  10. customthe residue obtained
  11. customwas purified by a silica-gel column chromatography
  12. customrecrystallized from methanol

Sources & evidence

ORD record
ord-7dda1eae56874d7eb4e7099a98ecb169
Source dataset
uspto-grants-1986_01
Patent number
US04567187

Reaction notes

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