Hydrochloric Acid → HCID 178428149, compound

HRID 1700593Notes

Reaction equation

HRID 1700593 reaction equation
[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]1[CH2:16][C:15]2[N:14]=[CH:13][CH:12]=[C:11]([CH3:17])[C:10]=2[C:9](=O)[CH2:8]1.[C:19]([NH:22][NH2:23])([NH2:21])=[NH:20].Cl.Cl.O>C(O)C>[ClH:1].[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]1[CH2:16][C:15]2[N:14]=[CH:13][CH:12]=[C:11]([CH3:17])[C:10]=2[C:9](=[N:23][NH:22][C:19]([NH2:21])=[NH:20])[CH2:8]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 18317361HCID 18317361, compoundHCID 178418668HCID 178418668, compound

Product 1

HCID 178428149HCID 178428149, compoundYield 115%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 7-(3-chloro-2-thienyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (0.3 g), aminoguanidine hydrochloride (0.14 g), concentrated hydrochloric acid (0.27 ml), water (0.27 ml) and ethanol (30 ml) was refluxed for 6 hours. Under reduced pressure, the solvent was evaporated, and to the residue was added water. The mixture was washed with ethyl acetate, and to the mixture was added sodium hydrogen carbonate solution. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in ethanol. To the solution was added a solution of 4N hydrochloric acid-ethyl acetate (0.4 ml), and the mixture was concentrated under reduced pressure. The resulting crystals were recrystallized from ethanol-water to give 7-(3-chloro-2-thienyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride (Compound 74) (0.23 g) as colorless crystals.

Workup

  1. temperaturewas refluxed for 6 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. additionto the mixture was added sodium hydrogen carbonate solution
  6. extractionThe mixture was extracted with ethyl acetate
  7. washthe organic layer was washed with water and saturated brine
  8. customUnder reduced pressure, the solvent was evaporated
  9. dissolutionthe residue was dissolved in ethanol
  10. additionTo the solution was added a solution of 4N hydrochloric acid-ethyl acetate (0.4 ml)
  11. concentrationthe mixture was concentrated under reduced pressure
  12. customThe resulting crystals were recrystallized from ethanol-water

Sources & evidence

ORD record
ord-e196b3bbe343470982b9dba8eae4ce0a
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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