Hydrochloric Acid → 7-(4-Fluorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride

HRID 1700596Notes

Reaction equation

HRID 1700596 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=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][C:5]([CH:8]2[CH2:17][C:16]3[N:15]=[CH:14][CH:13]=[C:12]([CH3:18])[C:11]=3[C:10](=[N:24][NH:23][C:20]([NH2:22])=[NH:21])[CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 183174737-(4-Fluorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-oneHCID 178418668HCID 178418668, compound

Product 1

HCID 1784281157-(4-Fluorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochlorideYield 62.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 7-(4-fluorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (0.2 g), aminoguanidine hydrochloride (0.091 g), concentrated hydrochloric acid (0.2 ml), water (0.2 ml) and ethanol (30 ml) was refluxed for 5 hours. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in water. The solution was washed with ethyl acetate. Under reduced pressure, the solvent was evaporated, and the residue was recrystallized from ethanol-ethyl acetate and then recrystallized from ethanol-water to give 7-(4-fluorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride (Compound 77) (0.17 g) as colorless crystals.

Workup

  1. temperaturewas refluxed for 5 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. customUnder reduced pressure, the solvent was evaporated
  6. customthe residue was recrystallized from ethanol-ethyl acetate
  7. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-7e7c2832f71d42a391a00e12a611680d
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

Loading…