Carbon Dioxide → Benzo[c]cinnoline

HRID 616521Notes

Reaction equation

HRID 616521 reaction equation
N([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N:16]=[N+:17]=[N-])=[N+]=[N-].C(O)C.C(=O)=O>OCC(CO)O>[CH:15]1[C:10]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:17]=[N:16][C:11]=2[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 702EthanolHCID 100370931,1'-Biphenyl, 2,2'-diazido-

Product 1

HCID 9190Benzo[c]cinnolineYield 52%

Reagents, catalysts & solvents 1

HCID 753GlycerolSolvent

Procedure

160 mg of 2,2'-diazidobiphenyl was dissolved in a small amount of diethyl ehter and then the solution thus obtained was dissolved in 500 ml of glycerol and the resultant solution was poured into a quarty cylindrical cell. The cell was dipped into a mixed coolant of ethyl alcohol and solid carbon dioxide to convert the solution to low-temperature rigid solution. The cell was irradiated with light in the same manner set forth in Example 1. After the irradiation, the cell was taken out of the coolant. After fluidized, the reaction product was extracted with 2l of diethyl ether. Diethyl ether was removed off by distillation. 62 mg of pure benzo[C]cinnoline was obtained by recrystallization of the residue using a mixed solvent of hexane and diethyl ether. Yield was about 52%.

Workup

  1. customthe solution thus obtained
  2. customThe cell was irradiated with light in the same manner
  3. customAfter the irradiation
  4. extractionthe reaction product was extracted with 2l of diethyl ether
  5. customDiethyl ether was removed off by distillation

Sources & evidence

ORD record
ord-589d8babecdd4dde8cb38ae48588fb18
Source dataset
uspto-grants-1978_02
Patent number
US04075074

Reaction notes

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