Hydrochloric Acid → HCID 178424169, compound

HRID 1700530Notes

Reaction equation

HRID 1700530 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][C:13]=3[CH3:18])[CH2:6][C:5]=2[NH:4][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:9]1[CH2:8][CH:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[CH2:6][C:5]2[NH:4][CH:3]=[C:2]([CH3:1])[C:10]1=2)[C:19]([NH2:21])=[NH:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 111074403-Methyl-6-(2-methylphenyl)-4,5,6,7-tetrahydroindol-4-oneHCID 178418668HCID 178418668, compound

Product 1

HCID 178424169HCID 178424169, compoundYield 4.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-methyl-6-(2-methylphenyl)-4,5,6,7-tetrahydroindol-4-one (0.70 g), aminoguanidine hydrochloride (0.34 g), concentrated hydrochloric acid (0.44 ml), water (0.44 ml) and ethanol (50 ml) was refluxed for 12 hours. Under reduced pressure, the solvent was evaporated. To the residue was added sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure, and the residue was purified with silica gel column chromatography (EtOAc/MeOH/Et3N). The resulting oil was dissolved in ethanol, and 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-3-methyl-6-(2-methylphenyl)-4,5,6,7-tetrahydroindole hydrochloride (Compound 6) (0.04 g) as colorless crystals.

Workup

  1. temperaturewas refluxed for 12 hours
  2. customUnder reduced pressure, the solvent was evaporated
  3. additionTo the residue was added sodium hydrogen carbonate solution
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customthe residue was purified with silica gel column chromatography (EtOAc/MeOH/Et3N)
  9. dissolutionThe resulting oil 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-a27b4e8c2a644b26843b70b10eda8be3
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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