2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 1397657, compound

HRID 973125Notes

Reaction equation

HRID 973125 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:21][CH:12]3[C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=4[C:19](=[O:20])[N:11]3[N:10]=2)=[CH:5][CH:4]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:21]=[C:12]3[C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=4[C:19](=[O:20])[N:11]3[N:10]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinone2×HCID 6241782-(4-Methoxyphenyl)-3,3a-dihydro-8H-pyrazolo[5,1-a]isoindol-8-one

Product 1

HCID 1397657HCID 1397657, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 62.00 g 2-(4-methoxyphenyl)-3,3a-dihydro-8-H-pyrazolo[5,1-a]isoindol-8-one, 1100 ml of benzene, and 27.2 g. of 2,3-dichloro-5,6-dicyanobenzoquinone was heated under reflux for 2 hours under nitrogen atmosphere. A further 27.2 g of 2,3-dichloro-5,6-dicyanobenzoquinone was added, and the heating was continued for a total of 8 hours. After cooling to 25°, the solid residue was filtered off, and the filtrate was evaporated to dryness under vacuum. The combined solids from the filter and evaporation flask were stirred mechanically for 1 hour with a mixture of 20 g of 85% potassium hydroxide and 1500 g of water. The mixture was filtered, the yellow solid was washed successively with 2 × 500-ml of 5% sodium bicarbonate, 2 × 500-ml of water, and air-dried. The yellow residue was recrystallized from 3000 ml of acetone to yield 55 g (80%) of 2-(4-methoxyphenyl)pyrazolo[5,1-a]isoindol-8-one, mp 180°-181°.

Workup

  1. temperatureunder reflux for 2 hours under nitrogen atmosphere
  2. customwas continued for a total of 8 hours
  3. temperatureAfter cooling to 25°
  4. filtrationthe solid residue was filtered off
  5. customthe filtrate was evaporated to dryness under vacuum
  6. filtrationThe combined solids from the filter
  7. customevaporation flask
  8. filtrationThe mixture was filtered
  9. washthe yellow solid was washed successively with 2 × 500-ml of 5% sodium bicarbonate, 2 × 500-ml of water
  10. customair-dried
  11. customThe yellow residue was recrystallized from 3000 ml of acetone

Sources & evidence

ORD record
ord-d3e841968e474fcea71937134593149b
Source dataset
uspto-grants-1977_10
Patent number
US04055409

Reaction notes

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