Hydrochloric Acid → HCID 178428108, compound

HRID 1700579Notes

Reaction equation

HRID 1700579 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:17][C:16]2[N:15]=[CH:14][CH:13]=[C:12]([CH3:18])[C:11]=2[C:10](=O)[CH2:9]1.[C:20]([NH:23][NH2:24])([NH2:22])=[NH:21].[ClH:25].Cl.O>C(O)C>[ClH:25].[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:17][C:16]2[N:15]=[CH:14][CH:13]=[C:12]([CH3:18])[C:11]=2[C:10](=[N:24][NH:23][C:20]([NH2:22])=[NH:21])[CH2:9]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10945005HCID 10945005, compoundHCID 178418668HCID 178418668, compound

Product 1

HCID 178428108HCID 178428108, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 7-(2-fluorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (0.35 g), aminoguanidine hydrochloride (0.16 g), concentrated hydrochloric acid (0.21 ml), water (0.21 ml) and ethanol (40 ml) was refluxed for 7 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 mixture was added sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. 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 dissolved in ethanol. To the solution was added 1N hydrochloric acid (3 ml), and the mixture was concentrated under reduced pressure. The residue was recrystallized from ethanol to give 7-(2-fluorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride (Compound 59) (0.33 g) as colorless crystals.

Workup

  1. temperaturewas refluxed for 7 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 mixture was added sodium hydrogen carbonate solution
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with water and saturated brine
  8. dry with materialdried with magnesium sulfate
  9. customUnder reduced pressure, the solvent was evaporated
  10. dissolutionthe residue was dissolved in ethanol
  11. additionTo the solution was added 1N hydrochloric acid (3 ml)
  12. concentrationthe mixture was concentrated under reduced pressure
  13. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-416aefa87b184a0e846ca4f8a7887b2e
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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