Hydrochloric Acid → 2-(4-aminophenyl)-9-chloro-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one

HRID 2231213Notes

Reaction equation

HRID 2231213 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]2[CH2:6][CH2:7][CH:8]3[C:13]([C:4]=2[CH:3]=1)=[N:12][N:11]([C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=1)[C:10](=[O:23])[CH2:9]3.Cl>C(O)C.O.[Fe]>[NH2:20][C:17]1[CH:18]=[CH:19][C:14]([N:11]2[C:10](=[O:23])[CH2:9][CH:8]3[C:13]([C:4]4[CH:3]=[C:2]([Cl:1])[CH:25]=[CH:24][C:5]=4[CH2:6][CH2:7]3)=[N:12]2)=[CH:15][CH:16]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 13712353HCID 13712353, compound

Product 1

HCID 212863822-(4-aminophenyl)-9-chloro-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a mixture of 9-chloro-2-(4-nitrophenyl)-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one in ethanol and water is added iron powder with stirring at room temperature. To the mixture is added dropwise concentrated hydrochloric acid with stirring and heating up to 60° C. on a water bath. The resulting mixture is further stirred under heating at the same temperature and filtered, then the filtrate is concentrated. After the residue is made alkaline by adding an aqueous solution of sodium hydroxide, the mixture is extracted with chloroform. The extract is washed with water and dried over magnesium sulfate anhydride. The chloroform is distilled off to give 2-(4-aminophenyl)-9-chloro-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one.

Workup

  1. stirringwith stirring
  2. temperatureheating up to 60° C. on a water bath
  3. stirringThe resulting mixture is further stirred
  4. temperatureunder heating at the same temperature
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated
  7. additionby adding an aqueous solution of sodium hydroxide
  8. extractionthe mixture is extracted with chloroform
  9. washThe extract is washed with water
  10. dry with materialdried over magnesium sulfate anhydride
  11. distillationThe chloroform is distilled off

Sources & evidence

ORD record
ord-2295e0beb3944337babecd0ec04fc791
Source dataset
uspto-grants-1988_11
Patent number
US04782057

Reaction notes

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