Hydrochloric Acid → 5-Guanidinoimino-4-methyl-7-(2-methylphenyl)-5,6,7,8-tetrahydroquinoline hydrochloride

HRID 1700577

Reaction equation

HRID 1700577 reaction equation
[CH3:1][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[CH3:19])[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.O>C(O)C>[ClH:25].[NH:23]([N:24]=[C:10]1[CH2:9][CH:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])[CH2:7][C:6]2[N:5]=[CH:4][CH:3]=[C:2]([CH3:1])[C:11]1=2)[C:20]([NH2:22])=[NH:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 109339624-Methyl-7-(2-methylphenyl)-5,6,7,8-tetrahydroquinolin-5-oneHCID 178418668HCID 178418668, compound

Product 1

HCID 1784241675-Guanidinoimino-4-methyl-7-(2-methylphenyl)-5,6,7,8-tetrahydroquinoline hydrochlorideYield 97.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-methyl-7-(2-methylphenyl)-5,6,7,8-tetrahydroquinolin-5-one (0.30 g), aminoguanidine hydrochloride (0.14 g), concentrated hydrochloric acid (0.018 ml), water (0.018 ml) and ethanol (30 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 concentrated under reduced pressure, and the residue was recrystallized from ethyl acetate-ethanol to give 5-guanidinoimino-4-methyl-7-(2-methylphenyl)-5,6,7,8-tetrahydroquinoline hydrochloride (Compound 57) (0.4 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. concentrationconcentrated under reduced pressure
  6. customthe residue was recrystallized from ethyl acetate-ethanol

Sources & evidence

ORD record
ord-b232cd63b9e548c9b3da057b24129de3
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Linked notes

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