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

HRID 1700590Notes

Reaction equation

HRID 1700590 reaction equation
[CH3:1][C:2]1[C:11]2[C:10](=O)[CH2:9][CH:8]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)[CH2:7][C:6]=2[N:5]=[CH:4][CH:3]=1.[C:18]([NH:21][NH2:22])([NH2:20])=[NH:19].[ClH:23].Cl.O>C(O)C>[ClH:23].[NH:21]([N:22]=[C:10]1[CH2:9][CH:8]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)[CH2:7][C:6]2[N:5]=[CH:4][CH:3]=[C:2]([CH3:1])[C:11]1=2)[C:18]([NH2:20])=[NH:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 109667404-Methyl-7-(2-thienyl)-5,6,7,8-tetrahydroquinolin-5-oneHCID 178418668HCID 178418668, compound

Product 1

HCID 1784281315-Guanidinoimino-4-methyl-7-(2-thienyl)-5,6,7,8-tetrahydroquinoline hydrochlorideYield 79.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-methyl-7-(2-thienyl)-5,6,7,8-tetrahydroquinolin-5-one (0.52 g), aminoguanidine hydrochloride (0.25 g), concentrated hydrochloric acid (0.53 ml), water (0.53 ml) and ethanol (50 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 diethylether and concentrated under reduced pressure, and the residue was recrystallized from water-ethanol to give 5-guanidinoimino-4-methyl-7-(2-thienyl)-5,6,7,8-tetrahydroquinoline hydrochloride (Compound 70) (0.57 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 diethylether
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was recrystallized from water-ethanol

Sources & evidence

ORD record
ord-58201ba36d854a95964566c4312154e8
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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