Hydrochloric Acid → HCID 178430222, compound

HRID 1700532Notes

Reaction equation

HRID 1700532 reaction equation
[CH3:1][N:2]1[C:10]2[CH2:9][CH:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:7][C:6](=O)[C:5]=2[C:4]([CH3:18])=[CH:3]1.[C:19]([NH:22][NH2:23])([NH2:21])=[NH:20].[ClH:24].Cl.O>C(O)C>[ClH:24].[NH:22]([N:23]=[C:6]1[CH2:7][CH:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:9][C:10]2[N:2]([CH3:1])[CH:3]=[C:4]([CH3:18])[C:5]1=2)[C:19]([NH2:21])=[NH:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 18317454HCID 18317454, compoundHCID 178418668HCID 178418668, compound

Product 1

HCID 178430222HCID 178430222, compoundYield 23.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1,3-dimethyl-6-phenyl-4,5,6,7-tetrahydroindol-4-one (0.31 g), aminoguanidine hydrochloride (0.15 g), concentrated hydrochloric acid (0.065 ml), water (0.065 ml) and ethanol (50 ml) was refluxed for 5 hours. 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 sodium hydrogen carbonate 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 1N hydrochloric acid. The solvent was evaporated, and the residue was recrystallized from ethanol-ethyl acetate to give 4-guanidinoimino-1,3-dimethyl-6-phenyl-4,5,6,7-tetrahydroindole hydrochloride (Compound 8) (0.1 g) as colorless crystals.

Workup

  1. temperaturewas refluxed for 5 hours
  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 sodium hydrogen carbonate 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 1N hydrochloric acid
  11. customThe solvent was evaporated
  12. customthe residue was recrystallized from ethanol-ethyl acetate

Sources & evidence

ORD record
ord-9f9f0562436b4bea9b39fd7a202f1f05
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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