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

HRID 1700587Notes

Reaction equation

HRID 1700587 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=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].[ClH:26].Cl.O>C(O)C>[ClH:26].[NH:24]([N:25]=[C:11]1[CH2:10][CH:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[CH2:18][C:17]2[N:16]=[CH:15][CH:14]=[C:13]([CH3:19])[C:12]1=2)[C:21]([NH2:23])=[NH:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 111190487-(2-Methoxyphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-oneHCID 178418668HCID 178418668, compound

Product 1

HCID 1784893085-Guanidinoimino-7-(2-methoxyphenyl)-4-methyl-5,6,7,8-tetrahydroquinoline hydrochlorideYield 55.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 7-(2-methoxyphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (0.40 g), aminoguanidine hydrochloride (0.17 g), concentrated hydrochloric acid (0.22 ml), water (0.22 ml) and ethanol (40 ml) was refluxed for 6 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. The residue was recrystallized from ethyl acetate-ethanol to give 5-guanidinoimino-7-(2-methoxyphenyl)-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride (Compound 67) (0.3 g) as colorless crystals.

Workup

  1. temperaturewas refluxed for 6 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-13483b8d0e074d8388c8d547cee28737
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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