Hydrochloric Acid → HCID 178423863, compound

HRID 1700605Notes

Reaction equation

HRID 1700605 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([CH3:12])[C:9]2[C:8](=O)[CH2:7][CH:6]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[CH2:5][C:4]=2[N: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:8]1[CH2:7][CH:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH2:5][C:4]2[N:3]=[C:2]([CH3:1])[CH:11]=[C:10]([CH3:12])[C:9]1=2)[C:20]([NH2:22])=[NH:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 183174342,4-Dimethyl-7-(2-pyridyl)-5,6,7,8-tetrahydroquinolin-5-oneHCID 178418668HCID 178418668, compound

Product 1

HCID 178423863HCID 178423863, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2,4-dimethyl-7-(2-pyridyl)-5,6,7,8-tetrahydroquinolin-5-one (0.08 g), aminoguanidine hydrochloride (0.037 g), concentrated hydrochloric acid (0.079 ml), water (0.079 ml) and ethanol (10 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. Under reduced pressure, the solvent was evaporated, and the residue was recrystallized from water-ethanol to give 5-guanidinoimino-2,4-dimethyl-7-(2-pyridyl)-5,6,7,8-tetrahydroquinoline hydrochloride (Compound 87) (0.1 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. customUnder reduced pressure, the solvent was evaporated
  6. customthe residue was recrystallized from water-ethanol

Sources & evidence

ORD record
ord-5027e1f831f44730bdf3b8eabb3b407a
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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