Hydrochloric Acid → 2H,5H-Spiro[imidazolidine-4,5'-indeno[1,2-b]pyridine]-2,5-dione

HRID 1903612Notes

Reaction equation

HRID 1903612 reaction equation
[CH:1]1[C:13]2[C:12](=O)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[N:4]=[CH:3][CH:2]=1.[C-]#N.[K+].[C:18](=[O:21])([O-])[O-].[NH4+:22].[NH4+:23].Cl.[CH2:25]([OH:27])C>>[NH:22]1[C:25](=[O:27])[C:12]2([C:13]3[CH:1]=[CH:2][CH:3]=[N:4][C:5]=3[C:6]3[C:11]2=[CH:10][CH:9]=[CH:8][CH:7]=3)[NH:23][C:18]1=[O:21]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 9032Potassium CyanideHCID 774895H-Indeno(1,2-b)pyridin-5-oneHCID 517111Ammonium Carbonate

Product 1

HCID 134913842H,5H-Spiro[imidazolidine-4,5'-indeno[1,2-b]pyridine]-2,5-dione

Procedure

4-Aza-9-fluorenone (Aldrich Chemical Co.), (2.4 g, 13.3 mmol), KCN (2.0 g, 30.7 mmol) and ammonium carbonate (5.0 g) in 80% ethanol (50 cc) were placed in a thick walled glass pressure reactor. The mixture was heated at 110°-115° C. for 12 hours. The reaction vessel was cooled and ice water (200 mL) was added to the reaction mixture. Dilute hydrochloric acid was added until pH was approximately 8 and the solid was collected by filtration. The collected solid was dissolved in 5% sodium hydroxide and treated with activated charcoal and filtered through a Celite (diatomaceous earth filter aid) pad. The solution was adjusted to pH 7-8 by the addition of 1 N hydrochloric acid. The resulting precipitate was collected on a filter, washed with cold water and dried to yield a sample of dl-Spiro-(4-aza-fluorene-9,4'-imidazolidine)-2',5'-dione (1.4 g) having a melting point of 311°-312° C. with dec., m/e+ . 251 for C14H9N3O2.

Workup

  1. temperatureThe mixture was heated at 110°-115° C. for 12 hours
  2. temperatureThe reaction vessel was cooled
  3. filtrationthe solid was collected by filtration
  4. dissolutionThe collected solid was dissolved in 5% sodium hydroxide
  5. additiontreated with activated charcoal
  6. filtrationfiltered through a Celite (diatomaceous earth filter aid) pad
  7. additionThe solution was adjusted to pH 7-8 by the addition of 1 N hydrochloric acid
  8. customThe resulting precipitate was collected on a filter
  9. washwashed with cold water
  10. customdried

Sources & evidence

ORD record
ord-f7732923cbb04115a7b5543aff4f4f88
Source dataset
uspto-grants-1984_03
Patent number
US04436745

Reaction notes

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