Hydrochloric Acid → HCID 178428148, compound

HRID 1700661Notes

Reaction equation

HRID 1700661 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][N: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][N: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 18317582HCID 18317582, compoundHCID 178418668HCID 178418668, compound

Product 1

HCID 178428148HCID 178428148, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-methyl-7-(2-thiazolyl)-5,6,7,8-tetrahydroquinolin-5-one (0.68 g), aminoguanidine hydrochloride (0.37 g), concentrated hydrochloric acid (0.7 ml), water (0.7 ml) and ethanol (25 ml) was refluxed for 5 hours. Under reduced pressure, the solvent was evaporated, and to the residue was added water. The mixture was washed with ethyl acetate. Under reduced pressure, the solvent was evaporated, and the residue was recrystallized from ethanol-water to give 5-guanidinoimino-4-methyl-7-(2-thiazolyl)-5,6,7,8-tetrahydroquinoline hydrochloride (Compound 118) (0.9 g) as colorless crystals.

Workup

  1. temperaturewas refluxed for 5 hours
  2. customUnder reduced pressure, the solvent was evaporated
  3. additionto the residue was added water
  4. washThe mixture was washed with ethyl acetate
  5. customUnder reduced pressure, the solvent was evaporated
  6. customthe residue was recrystallized from ethanol-water

Sources & evidence

ORD record
ord-fe7d4f716e514085a61b876dd26cb80e
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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