Hydrochloric Acid → HCID 178466910, compound

HRID 1700599Notes

Reaction equation

HRID 1700599 reaction equation
[Cl:1][C:2]1[C:11]2[C:10](=O)[CH2:9][CH:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[CH2:7][C:6]=2[N:5]=[CH:4][CH:3]=1.[C:20]([NH:23][NH2:24])([NH2:22])=[NH:21].[ClH:25].Cl.[OH2:27].[CH2:28]([OH:30])[CH3:29]>>[ClH:1].[Cl:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH:8]1[CH2:7][C:6]2[N:5]=[CH:4][CH:3]=[C:2]([O:30][CH2:28][CH3:29])[C:11]=2[C:10](=[N:24][NH:23][C:20]([NH2:22])=[NH:21])[CH2:9]1.[ClH:25].[Cl:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH:8]1[CH2:7][C:6]2[NH:5][CH:4]=[CH:3][C:2](=[O:27])[C:11]=2[C:10](=[N:24][NH:23][C:20]([NH2:22])=[NH:21])[CH2:9]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 183177884-Chloro-7-(2-chlorophenyl)-5,6,7,8-tetrahydroquinolin-5-oneHCID 178418668HCID 178418668, compound

Product 2

HCID 178466910HCID 178466910, compoundHCID 178479518HCID 178479518, compound

Conditions

Temperature
50 °C

Procedure

A mixture of 4-chloro-7-(2-chlorophenyl)-5,6,7,8-tetrahydroquinolin-5-one (0.1 g), aminoguanidine hydrochloride (0.040 g), concentrated hydrochloric acid (0.034 ml), water (0.034 ml) and ethanol (20 ml) was stirred at room temperature for 30 minutes and at 50° C. for 5 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 solution was added sodium hydrogen carbonate solution. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column chromatography (EtOAc/MeOH/Et3N). To the resulting two kinds of amorphous was added 1N hydrochloric acid and concentrated to give 7-(2-chlorophenyl)-4-ethoxy-5-guanidinoimino-5,6,7,8-tetrahydroquinoline hydrochloride (Compound 80) (0.05 g) as colorless crystals and 7-(2-chlorophenyl)-5-guanidinoimino-1,4,5,6,7,8-hexahydroquinoline-4-one hydrochloride (Compound 81) (0.04 g) as amorphous, respectively.

Workup

  1. customUnder reduced pressure, the solvent was evaporated
  2. dissolutionthe residue was dissolved in water
  3. washThe solution was washed with ethyl acetate
  4. additionto the solution was added sodium hydrogen carbonate solution
  5. extractionThe mixture was extracted with ethyl acetate
  6. washthe organic layer was washed with water and saturated brine
  7. dry with materialdried with magnesium sulfate
  8. customUnder reduced pressure, the solvent was evaporated
  9. customthe residue was purified with silica gel column chromatography (EtOAc/MeOH/Et3N)
  10. additionTo the resulting two kinds of amorphous was added 1N hydrochloric acid
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-c855d04721c74bf1adf097efc43fadcf
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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