Hydrochloric Acid → HCID 178423865, compound

HRID 49209Notes

Reaction equation

HRID 49209 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:21])=[C:6]([CH:8]2[CH2:17][C:16]3[N:15]=[C:14]([CH3:18])[CH:13]=[C:12]([CH3:19])[C:11]=3[C:10](=O)[CH2:9]2)[CH:7]=1.[C:22]([NH:25][NH2:26])([NH2:24])=[NH:23].[ClH:27].Cl.O>C(O)C>[ClH:27].[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:21])=[C:6]([CH:8]2[CH2:17][C:16]3[N:15]=[C:14]([CH3:18])[CH:13]=[C:12]([CH3:19])[C:11]=3[C:10](=[N:26][NH:25][C:22]([NH2:24])=[NH:23])[CH2:9]2)[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 178239227-(5-Fluoro-2-methylphenyl)-2,4-dimethyl-5,6,7,8-tetrahydroquinolin-5-oneHCID 178418668HCID 178418668, compound

Product 1

HCID 178423865HCID 178423865, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 7-(5-fluoro-2-methylphenyl)-2,4-dimethyl-5,6,7,8-tetrahydroquinolin-5-one (1.1 g) and aminoguanidine hydrochloride (0.52 g) in ethanol (30 ml) was combined with concentrated hydrochloric acid (1.0 ml) and water (1.0 ml), and the mixture was heated under reflux for 12 hours. The mixture was concentrated under reduced pressure, and the residue was recrystallized from ethanol to obtain 7-(5-fluoro-2-methylphenyl)-5-guanidinoimino-2,4-dimethyl-5,6,7,8-tetrahydroquinoline hydrochloride (Compound L) (1.25 g) as a colorless crystal.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 12 hours
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-64e873b8f5a347d4b56ecd439a8f108c
Source dataset
uspto-grants-2004_03
Patent number
US06706732B1

Reaction notes

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