Hydrochloric Acid → HCID 21286386, compound

HRID 2231218Notes

Reaction equation

HRID 2231218 reaction equation
[N+:1]([C:4]1[CH:24]=[CH:23][C:7]2[CH2:8][CH2:9][CH:10]3[C:15]([C:6]=2[CH:5]=1)=[N:14][N:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:12](=[O:22])[CH2:11]3)([O-])=O.Cl>C(O)C.O.[Fe]>[NH2:1][C:4]1[CH:24]=[CH:23][C:7]2[CH2:8][CH2:9][CH:10]3[C:15]([C:6]=2[CH:5]=1)=[N:14][N:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:12](=[O:22])[CH2:11]3

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 21286379HCID 21286379, compound

Product 1

HCID 21286386HCID 21286386, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a mixture of 9-nitro-2-phenyl-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one in ethanol and water is added iron powder with stirring at room temperature. The mixture is heated up to 50° C. on a water bath with stirring and concentrated hydrochloric acid is added dropwise carefully. The resulting mixture is further stirred with heating at 80° C. and the filtrate is concentrated. To the residue is added an aqueous sodium hydroxide solution, and the alkaline solution is extracted with chloroform. The extract is washed with water, dried over magnesium sulfate anhydride and the chloroform is distilled off to give 9-amino-2-phenyl-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one.

Workup

  1. temperatureThe mixture is heated up to 50° C. on a water bath
  2. stirringwith stirring
  3. stirringThe resulting mixture is further stirred
  4. temperaturewith heating at 80° C.
  5. concentrationthe filtrate is concentrated
  6. additionTo the residue is added an aqueous sodium hydroxide solution
  7. extractionthe alkaline solution is extracted with chloroform
  8. washThe extract is washed with water
  9. dry with materialdried over magnesium sulfate anhydride
  10. distillationthe chloroform is distilled off

Sources & evidence

ORD record
ord-9b849edc950e4c14b29c041b1f79b68b
Source dataset
uspto-grants-1988_11
Patent number
US04782057

Reaction notes

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