Hydrochloric Acid → HCID 178428122, compound

HRID 1700755Notes

Reaction equation

HRID 1700755 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:20])=[C:6]([CH:8]2[CH2:17][C:16]3[N:15]=[CH:14][CH:13]=[C:12]([CH3:18])[C:11]=3[C:10](=O)[CH2:9]2)[CH:7]=1.[C:21]([NH:24][NH2:25])([NH2:23])=[NH:22].Cl.C(O)C.Cl>O>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:20])=[C:6]([CH:8]2[CH2:17][C:16]3[N:15]=[CH:14][CH:13]=[C:12]([CH3:18])[C:11]=3[C:10](=[N:25][NH:24][C:21]([NH2:23])=[NH:22])[CH2:9]2)[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 18317642HCID 18317642, compoundHCID 178418668HCID 178418668, compound

Product 1

HCID 178428122HCID 178428122, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 7-(5-chloro-2-hydroxyphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one were added aminoguanidine hydrochloride (0.53 g), ethanol (30 ml), concentrated hydrochloric acid (1.0 ml) and water (1.0 ml), and the mixture was refluxed for 4 hours. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in water. The solution was washed with ethyl acetate, and to the aqueous layer was added sodium hydrogen carbonate solution to make the solution alkaline. The solution was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in ethanol, and to the solution was added 1N hydrochloric acid (10 ml). The mixture was concentrated, and precipitated crystals were recrystallized from ethanol to give 7-(5-chloro-2-hydroxyphenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride (Compound 167) (1.1 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 solution was washed with ethyl acetate
  5. additionto the aqueous layer was added sodium hydrogen carbonate solution
  6. extractionThe solution was extracted with ethyl acetate
  7. washthe organic layer was washed with water and saturated brine
  8. dry with materialdried with magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. dissolutionThe residue was dissolved in ethanol
  11. additionto the solution was added 1N hydrochloric acid (10 ml)
  12. concentrationThe mixture was concentrated
  13. customprecipitated crystals
  14. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-87f50b4891594c498fbc3badb98bd0aa
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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