Hydrochloric Acid → HCID 178428124, compound

HRID 1700653Notes

Reaction equation

HRID 1700653 reaction equation
[Cl:1][C:2]1[S:3][C:4]([Cl:19])=[CH:5][C:6]=1[CH:7]1[CH2:16][C:15]2[N:14]=[CH:13][CH:12]=[C:11]([CH3:17])[C:10]=2[C:9](=O)[CH2:8]1.[C:20]([NH:23][NH2:24])([NH2:22])=[NH:21].Cl.Cl.O>C(O)C>[ClH:1].[Cl:1][C:2]1[S:3][C:4]([Cl:19])=[CH:5][C:6]=1[CH:7]1[CH2:16][C:15]2[N:14]=[CH:13][CH:12]=[C:11]([CH3:17])[C:10]=2[C:9](=[N:24][NH:23][C:20]([NH2:22])=[NH:21])[CH2:8]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 183173437-(2,5-Dichlorothiophen-3-yl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-oneHCID 178418668HCID 178418668, compound

Product 1

HCID 178428124HCID 178428124, compoundYield 207.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (10 ml) was dissolved (−)-7-(2,5-dichlorothiophen-3-yl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (0.35 g), and to the mixture were added aminoguanidine hydrochloride (0.15 g), concentrated hydrochloric acid (0.28 ml) and water (0.28 ml). The mixture was refluxed for 4 hours, and under reduced pressure, the solvent was evaporated. The residue was dissolved in water, and the mixture was washed with ethyl acetate and concentrated under reduced pressure. The residue was heated in a little amount of ethanol, and the solution was cooled. Precipitated crystals were filtered off, and the mother liquor was concentrated to give crystals, which were recrystallized from water to give (−)-7-(2,5-dichlorothiophen-3-yl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride (Compound 109) (0.47 g) as colorless crystals.

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. customunder reduced pressure, the solvent was evaporated
  3. dissolutionThe residue was dissolved in water
  4. washthe mixture was washed with ethyl acetate
  5. concentrationconcentrated under reduced pressure
  6. temperatureThe residue was heated in a little amount of ethanol
  7. temperaturethe solution was cooled
  8. customPrecipitated crystals
  9. filtrationwere filtered off
  10. concentrationthe mother liquor was concentrated
  11. customto give crystals, which
  12. customwere recrystallized from water

Sources & evidence

ORD record
ord-63e0283585cc4a87a25cdd5bbc035900
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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