HCID 2823732, compound → Benzo[c]cinnoline, 3,8-dimethyl-

HRID 2286418Notes

Reaction equation

HRID 2286418 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:9]=2[N+:15]([O-])=O)=[C:4]([N+:18]([O-])=O)[CH:3]=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:9]=3[N:15]=[N:18][C:4]=2[CH:3]=1

Participants

3

Reactant 1

HCID 2823732HCID 2823732, compound

Product 1

HCID 12201755Benzo[c]cinnoline, 3,8-dimethyl-

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

64 g (0.235 mol) of 4,4'-dimethyl-2,2'-dinitrobiphenyl are dissolved in 700 ml of dry toluene, under argon. 313 g (1.084 mols) of sodium dihydro-bis-(2-methoxyethoxy)-aluminate (70% in toluene) are added slowly dropwise, with stirring; an exothermic reaction takes place. The mixture is stirred for a further 10 minutes at about 80° C. The solution is evaporated to dryness. The oily residue is ground with 500 ml of water and 100 ml of concentrated ammonia. The brown suspension is filtered through a glass filter and the precipitate is washed with water. The precipitate is then extracted with ethanol in a Soxhlet apparatus for 5 days. The resulting alcoholic solution is refluxed with active charcoal and filtered hot and the filtrate is evaporated to dryness. The crude product thus obtained is finally recrystallised from a mixture of toluene/isooctane.

Workup

  1. customan exothermic reaction
  2. stirringThe mixture is stirred for a further 10 minutes at about 80° C
  3. customThe solution is evaporated to dryness
  4. filtrationThe brown suspension is filtered through a glass
  5. filtrationfilter
  6. washthe precipitate is washed with water
  7. extractionThe precipitate is then extracted with ethanol in a Soxhlet apparatus for 5 days
  8. temperatureThe resulting alcoholic solution is refluxed with active charcoal
  9. filtrationfiltered hot
  10. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-c54934ebef424c7fa917006183bb4aed
Source dataset
uspto-grants-1981_05
Patent number
US04266011

Reaction notes

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