Water → Spiro[imidazolidin-4,4'-pyrano[3,2-h]quinolin]-2,5-dione

HRID 47057Notes

Reaction equation

HRID 47057 reaction equation
[C-:1]#[N:2].[K+].[C:4](=[O:7])([O-])[O-].[NH4+:8].[NH4+].[O:10]1[C:23]2[C:22]3[N:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH:16]=[CH:15][C:14]=2[C:13](=O)[CH:12]=[CH:11]1.[OH2:25]>C(O)C>[O:10]1[C:23]2[C:22]3[N:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH:16]=[CH:15][C:14]=2[C:13]2([C:1](=[O:25])[NH:2][C:4](=[O:7])[NH:8]2)[CH:12]=[CH:11]1

Participants

6

Reactant 4

HCID 962Water2×HCID 9032Potassium CyanideHCID 517111Ammonium CarbonateHCID 20385028HCID 20385028, compound

Product 1

HCID 20385032Spiro[imidazolidin-4,4'-pyrano[3,2-h]quinolin]-2,5-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 0.500 g (2.51 mmol) of potassium cyanide and 0.280 g (4.27 mmol) of ammonium carbonate in 1.5 ml water was added to a solution of 130 mg (0.65 mmol) of pyrano[3,2-h]quinolin-4-one in 1.5 ml of ethanol at 60° C. The reaction mixture was held at this temperature for 72 hours then added to 20 ml of water and boiled for 20 minutes. The basic mixture was extracted with 3×50 ml chloroform and the mixture was acidified with 1 N hydrochloric acid. The solid obtained after filtration and drying in vacuo (96 mg) was twice recrystallized from ethanol yielding spiro[imidazolidin-4,4'-pyrano[3,2-h]quinolin]-2,5-dione, (36.0 mg), m.p. 305° C. (dec).

Workup

  1. waitboiled for 20 minutes
  2. extractionThe basic mixture was extracted with 3×50 ml chloroform
  3. customThe solid obtained
  4. filtrationafter filtration
  5. customdrying in vacuo (96 mg)
  6. customwas twice recrystallized from ethanol

Sources & evidence

ORD record
ord-0e739c2b68924cbba76a2337c7de84f0
Source dataset
uspto-grants-1979_11
Patent number
US04176185

Reaction notes

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