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

HRID 2413476Notes

Reaction equation

HRID 2413476 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[C:7](=O)[C:8]3[C:13]([C:2]=12)=[CH:12][CH:11]=[CH:10][CH:9]=3.[C-]#N.[K+].[C:18](=[O:21])([O-])[O-].[NH4+:22].[NH4+:23].Cl.[CH2:25]([OH:27])C>O>[NH:22]1[C:25](=[O:27])[C:7]2([C:3]3[C:2](=[N:1][CH:6]=[CH:5][CH:4]=3)[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:23][C:18]1=[O:21]

Participants

7

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
105 °C

Procedure

5H-Indeno[1,2-b]pyridine-5-one (4.0 g, 22 mmol) was mixed with potassium cyanide (1.6 g, 24 mmol) and ammonium carbonate (5.3 g, 55 mmol) in 90% ethanol (75 mL) in a pressure reactor and heated at 105° C. for 40 hr. The mixture was poured into 300 mL of water, acidified with conc. HCl (pH 1), and filtered. The filtrate was neutralized and the solid which formed collected by filtration, washed with water, and dried to yield 4.5 g. This solid was crystallized from ethyl acetate to yield 3.2 g of product. (This material was no longer soluble in ethyl acetate after the first crystallization). m/e+· 251.

Workup

  1. filtrationfiltered
  2. customthe solid which formed
  3. filtrationcollected by filtration
  4. washwashed with water
  5. customdried
  6. customto yield 4.5 g
  7. customThis solid was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-2e16fd9b0b364b0c836db457e2e39f8a
Source dataset
uspto-grants-1988_01
Patent number
US04717725

Reaction notes

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