Hydrochloric Acid → HCID 178428117, compound

HRID 1700580Notes

Reaction equation

HRID 1700580 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=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].[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:18][C:17]2[N:16]=[CH:15][CH:14]=[C:13]([CH3:19])[C:12]=2[C:11](=[N:25][NH:24][C:21]([NH2:23])=[NH:22])[CH2:10]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 18317593HCID 18317593, compoundHCID 178418668HCID 178418668, compound

Product 1

HCID 178428117HCID 178428117, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 7-(2,4-difluorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (0.43 g), aminoguanidine hydrochloride (0.18 g), concentrated hydrochloric acid (0.39 ml), water (0.39 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 ethyl acetate, and the mixture was concentrated under reduced pressure. The residue was recrystallized from water-ethanol to give 7-(2,4-difluorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride (Compound 60) (0.45 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. concentrationthe mixture was concentrated under reduced pressure
  6. customThe residue was recrystallized from water-ethanol

Sources & evidence

ORD record
ord-4705b0cdd2814419a71bfb5ddf0cf1de
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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