Hydrochloric Acid → HCID 178426011, compound

HRID 49192Notes

Reaction equation

HRID 49192 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:20])=[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].[ClH:26].Cl.O>C(O)C>[ClH:26].[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:20])=[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 962WaterHCID 110219267-(5-Fluoro-2-methylphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-oneHCID 178418668HCID 178418668, compound

Product 1

HCID 178426011HCID 178426011, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 7-(5-fluoro-2-methylphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (1.1 g) and aminoguanidine hydrochloride (0.54 g) in ethanol (30 ml) was combined with concentrated hydrochloric acid (1.0 ml) and water (1.0 ml) and heated under reflux for 6 hours. The solvent was distilled off under reduced pressure, and the residue was dissolved in water and washed with ethyl acetate. The aqueous layer was made alkaline with aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in ethanol, combined with 1N hydrochloric acid (10 ml) and concentrated, and then the precipitated crystal was recrystallized from ethanol to obtain 7-(5-fluoro-2-methylphenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride (Compound C) (1.4 g) as a colorless crystal.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 6 hours
  3. distillationThe solvent was distilled off under reduced pressure
  4. dissolutionthe residue was dissolved in water
  5. washwashed with ethyl acetate
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed successively with water and saturated brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. dissolutionThe residue was dissolved in ethanol
  11. concentrationconcentrated
  12. customthe precipitated crystal was recrystallized from ethanol

Sources & evidence

ORD record
ord-d4e4d62a14d343c6b3e41c0ec06eed71
Source dataset
uspto-grants-2004_03
Patent number
US06706732B1

Reaction notes

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