Hydrochloric Acid → HCID 178430811, compound

HRID 1700526Notes

Reaction equation

HRID 1700526 reaction equation
[CH3:1][C:2]1[C:10]2[C:9](=O)[CH2:8][CH:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:6][C:5]=2[NH:4][CH:3]=1.[C:18]([NH:21][NH2:22])([NH2:20])=[NH:19].[ClH:23].Cl.O>C(O)C>[ClH:23].[NH:21]([N:22]=[C:9]1[CH2:8][CH:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6][C:5]2[NH:4][CH:3]=[C:2]([CH3:1])[C:10]1=2)[C:18]([NH2:20])=[NH:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 183173703-Methyl-6-phenyl-4,5,6,7-tetrahydroindol-4-oneHCID 178418668HCID 178418668, compound

Product 1

HCID 178430811HCID 178430811, compoundYield 8.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-methyl-6-phenyl-4,5,6,7-tetrahydroindol-4-one (0.8 g), aminoguanidine hydrochloride (0.41 g), concentrated hydrochloric acid (0.18 ml), water (0.18 ml) and ethanol (50 ml) was refluxed for 30 minutes. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in water. The solution was washed with diethylether. To the mixture was added sodium hydroxide solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and to the residue was 1N hydrochloric acid (2 ml). The solvent was evaporated, and the residue was recrystallized from ethanol-ethyl acetate to give 4-guanidinoimino-3-methyl-6-phenyl-4,5,6,7-tetrahydroindole hydrochloride (Compound 2) (0.1 g) as colorless crystals.

Workup

  1. temperaturewas refluxed for 30 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 sodium hydroxide solution
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with water and saturated brine
  8. dry with materialdried with magnesium sulfate
  9. customUnder reduced pressure, the solvent was evaporated
  10. customThe solvent was evaporated
  11. customthe residue was recrystallized from ethanol-ethyl acetate

Sources & evidence

ORD record
ord-5bb786c6206446c897c7ad1c9cb5e800
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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