Hydrochloric Acid → HCID 178422197, compound

HRID 1700528Notes

Reaction equation

HRID 1700528 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[CH2:5][CH:6]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:7][C:8](=O)[C:9]=2[CH:10]=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:8]1[CH2:7][CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:5][C:4]2[NH:3][C:2]([CH3:1])=[CH:10][C:9]1=2)[C:18]([NH2:20])=[NH:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 18317565HCID 18317565, compoundHCID 178418668HCID 178418668, compound

Product 1

HCID 178422197HCID 178422197, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-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 1 hour. Under reduced pressure, the solvent was evaporated. The residue was suspended in ethyl acetate, and the suspension was washed with water. Under reduced pressure, the solvent was evaporated. The residue 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-2-methyl-6-phenyl-4,5,6,7-tetrahydroindole hydrochloride (Compound 4) (0.92 g) as colorless crystals.

Workup

  1. temperaturewas refluxed for 1 hour
  2. customUnder reduced pressure, the solvent was evaporated
  3. washthe suspension was washed with water
  4. customUnder reduced pressure, the solvent was evaporated
  5. dissolutionThe residue was dissolved in ethanol
  6. additionto the solution was added 1N hydrochloric acid
  7. customThe solvent was evaporated
  8. customthe residue was recrystallized from ethanol-ethyl acetate

Sources & evidence

ORD record
ord-4d2f83c33ccd4fafacc9303b21eaf7df
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

Loading…