2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 13934597, compound

HRID 649563Notes

Reaction equation

HRID 649563 reaction equation
[C:1]1([N:7]2[C:16]3[N:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:10]3[O:17][CH2:18][CH2:19][C:9]=3[C:8]2=[O:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1>[C:1]1([N:7]2[C:16]3[N:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:10]3[O:17][CH:18]=[CH:19][C:9]=3[C:8]2=[O:20])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 13934590HCID 13934590, compound

Product 1

HCID 13934597HCID 13934597, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3,5-dihydro-5-phenyl-furo-[3,2-c][1,8]-naphthyridin-4[2H]-one (2 g.) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ; 2 g.) in dry toluene (50 ml.) was stirred in an atmosphere of nitrogen and heated to reflux. Refluxing was continued for 20 hrs. After cooling somewhat the mixture was evaporated, dissolved in CH2Cl2, filtered and chromatographed on silica gel eluting with increasing concentrations of ethyl acetate in CH2Cl2 (0-10%). Evaporation of the relevant fractions and recrystallization from acetonitrile yielded the desired product, m.p. 245°-247° C.

Workup

  1. temperatureheated to reflux
  2. temperatureRefluxing
  3. temperatureAfter cooling somewhat the mixture
  4. customwas evaporated
  5. dissolutiondissolved in CH2Cl2
  6. filtrationfiltered
  7. customchromatographed on silica gel eluting
  8. temperaturewith increasing concentrations of ethyl acetate in CH2Cl2 (0-10%)
  9. customEvaporation of the relevant fractions and recrystallization from acetonitrile

Sources & evidence

ORD record
ord-46b205dc75bc4b9884943f5fb11ae991
Source dataset
uspto-grants-1988_04
Patent number
US04740511

Reaction notes

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