Hydrochloric Acid → HCID 13575822, compound

HRID 1981570Notes

Reaction equation

HRID 1981570 reaction equation
[C-]#N.[K+].Cl.O.COC([CH:10]1[C:14]2([C:24]3=[C:25]4[C:20](=[CH:21][CH:22]=[CH:23]3)[CH2:19][CH2:18][CH2:17][N:16]4[C:15]2=[O:26])[C:13](=[O:27])[NH:12][C:11]1=[O:28])=O>CO>[C:14]12([CH2:10][C:11](=[O:28])[NH:12][C:13]1=[O:27])[C:24]1=[C:25]3[C:20](=[CH:21][CH:22]=[CH:23]1)[CH2:19][CH2:18][CH2:17][N:16]3[C:15]2=[O:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 9032Potassium CyanideHCID 23319623HCID 23319623, compound

Product 1

HCID 13575822HCID 13575822, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of ethyl α-cyano-5,6-dihydro-2-oxo-Δ1,α -4H-pyrrolo[3,2,1-ij]quinolineacetate (8.47 g, 0.03 mole) in methanol (30 ml) was added potassium cyanide (2.93 g, 0.04 mole) and the mixture was stirred for 3 hours room temperature. The resultant solution was cooled to 0° C., saturated with hydrogen chloride gas and allowed to stand overnight. The mixture was warmed at 50° C. for an hour and refluxed for 4 hours. After cooling, an addition of water (30 ml) gave a viscous tar containing 4-methoxycarbonyl-5',6'-dihydrospiro[pyrrolidine-3,1'-[4H]pyrrolo[3,2,1-ij]quinoline]-2,2',5(1'H)-trione, which was extracted with benzene, washed with water and dried. Evaporation of the benzene afforded yellow oily residue, to which was added 40 ml of acetic acid and refluxed for 10 hours. After evaporation of the solvent, the residue was treated with benzene to give a fine solid. Recrystallization from ethanol yielded 2.92 g (38.0%) of 5',6'-dihydrospiro[pyrrolidine-3,1'-[4H]pyrrolo[3,2,1-ij]quinoline]-2,2',5(1'H)-trione, as colorless needles, mp. 253°-255° C.

Workup

  1. waitto stand overnight
  2. temperatureThe mixture was warmed at 50° C. for an hour
  3. temperaturerefluxed for 4 hours
  4. temperatureAfter cooling
  5. customgave a viscous tar
  6. extractionwas extracted with benzene
  7. washwashed with water
  8. customdried
  9. customEvaporation of the benzene afforded yellow oily residue
  10. additionto which was added 40 ml of acetic acid
  11. temperaturerefluxed for 10 hours
  12. customAfter evaporation of the solvent
  13. additionthe residue was treated with benzene
  14. customto give a fine solid
  15. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-569c1ce76717493ea894978cbd7b6d9a
Source dataset
uspto-grants-1986_06
Patent number
US04593092

Reaction notes

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