Hydrochloric Acid → 9H-Fluoren-9-one, 2,7-diamino-

HRID 1241223Notes

Reaction equation

HRID 1241223 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][C:10]([N+:17]([O-])=O)=[CH:11][CH:12]=3)[C:7](=[O:20])[C:6]=2[CH:5]=1)([O-])=O.Cl>C(O)(=O)C>[NH2:1][C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][C:10]([NH2:17])=[CH:11][CH:12]=3)[C:7](=[O:20])[C:6]=2[CH:5]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 358422,7-Dinitro-9H-fluoren-9-one

Product 1

HCID 972389H-Fluoren-9-one, 2,7-diamino-

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2,7-Dinitro-9-fluorenone (162 g, 0.6 mol, from Aldrich) was added cautiously to a solution of hydrated stannous chloride (1100 g, 4.9 mol, from Aldrich) in a mixture of concentrated hydrochloric acid (900 ml) and acetic acid (1600 ml). The suspension was stirred and refluxed for 1 hour. The mixture was cooled to room temperature, and a solid appeared. The solid was harvested by filtration. The solid was washed first with concentrated hydrochloric acid, and then with water until the filtrate color was violet. The residue was dissolved in boiling water. The solution was filtered and then made alkaline with sodium hydroxide to from a precipitate. The precipitate was washed with water, dried, and recrystallized from dioxane. The yield of 2,7-diamino-9-fluorenone was 108 g (85.7%). The melting point was found to be 284–286° C.

Workup

  1. temperaturerefluxed for 1 hour
  2. filtrationThe solid was harvested by filtration
  3. washThe solid was washed first with concentrated hydrochloric acid
  4. dissolutionThe residue was dissolved
  5. filtrationThe solution was filtered
  6. washThe precipitate was washed with water
  7. customdried
  8. customrecrystallized from dioxane
  9. customto be 284–286° C.

Sources & evidence

ORD record
ord-e15ba46c9c9d4874b664005182bcc2de
Source dataset
uspto-grants-2006_10
Patent number
US07115347B2

Reaction notes

Loading…