Hydrochloric Acid → HCID 178479514, compound

HRID 1700525Notes

Reaction equation

HRID 1700525 reaction equation
[C:1]1([CH:7]2[CH2:15][C:14]3[NH:13][CH:12]=[CH:11][C:10]=3[C:9](=O)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]([NH:20][NH2:21])([NH2:19])=[NH:18].[ClH:22].Cl.O>C(O)C>[ClH:22].[NH:20]([N:21]=[C:9]1[CH2:8][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:15][C:14]2[NH:13][CH:12]=[CH:11][C:10]1=2)[C:17]([NH2:19])=[NH:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11052946HCID 11052946, compoundHCID 178418668HCID 178418668, compound

Product 1

HCID 178479514HCID 178479514, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-phenyl-4,5,6,7-tetrahydroindol-4-one (0.11 g), aminoguanidine hydrochloride (0.06 g), concentrated hydrochloric acid (0.026 ml), water (0.026 ml) and ethanol (10 ml) was refluxed for 20 minutes. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in water. The solution was washed with diethylether, and to the mixture was added 1N sodium hydroxide solution. The mixture was extracted with ethyl acetate, and the organic layer was dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in ethanol. To the solution was added 4N hydrochloric acid, and the solvent was evaporated. The residue was recrystallized from ethanol to give 4-guanidinoimino-6-phenyl-4,5,6,7-tetrahydroindole hydrochloride (Compound 1) (70 mg) as colorless crystals.

Workup

  1. temperaturewas refluxed for 20 minutes
  2. customUnder reduced pressure, the solvent was evaporated
  3. dissolutionthe residue was dissolved in water
  4. washThe solution was washed with diethylether
  5. additionto the mixture was added 1N sodium hydroxide solution
  6. extractionThe mixture was extracted with ethyl acetate
  7. dry with materialthe organic layer was dried with magnesium sulfate
  8. customUnder reduced pressure, the solvent was evaporated
  9. dissolutionthe residue was dissolved in ethanol
  10. additionTo the solution was added 4N hydrochloric acid
  11. customthe solvent was evaporated
  12. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-7bc3625dee034207bb645047280c4976
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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