Hydrochloric Acid → HCID 178428133, compound

HRID 49198Notes

Reaction equation

HRID 49198 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]1[CH2:18][C:17]2[N:16]=[CH:15][CH:14]=[C:13]([CH3:19])[C:12]=2[C:11](=O)[CH2:10]1.[C:21]([NH:24][NH2:25])([NH2:23])=[NH:22].Cl.Cl.O>C(O)C>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]1[CH2:18][C:17]2[N:16]=[CH:15][CH:14]=[C:13]([CH3:19])[C:12]=2[C:11](=[N:25][NH:24][C:21]([NH2:23])=[NH:22])[CH2:10]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 117482737-(2-Chloro-5-fluorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-oneHCID 178418668HCID 178418668, compound

Product 1

HCID 178428133HCID 178428133, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 7-(2-chloro-5-fluorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one in ethanol (10 ml) was combined with aminoguanidine hydrochloride (0.041 g), concentrated hydrochloric acid (0.078 ml) and water (0.078 ml), and the mixture was heated under reflux for 4 hours. The solvent was distilled off under reduced pressure, and the residue was combined with water and the aqueous layer was 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 1N hydrochloric acid (1 ml) and concentrated. The resultant crystal was recrystallized from ethanol-ethyl acetate to obtain 7-(2-chloro-5-fluorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride (Compound G) (0.05 g) as a colorless crystal.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. distillationThe solvent was distilled off under reduced pressure
  4. washthe aqueous layer was washed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed successively with water and saturated brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. dissolutionThe residue was dissolved in 1N hydrochloric acid (1 ml)
  10. concentrationconcentrated
  11. customThe resultant crystal was recrystallized from ethanol-ethyl acetate

Sources & evidence

ORD record
ord-95fab42f68de4fb9a9a1fcd6b5d81751
Source dataset
uspto-grants-2004_03
Patent number
US06706732B1

Reaction notes

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