Hydrochloric Acid → HCID 178428110, compound

HRID 1700588Notes

Reaction equation

HRID 1700588 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:17][C:16]2[N:15]=[CH:14][CH:13]=[C:12]([CH3:18])[C:11]=2[C:10](=O)[CH2:9]1.[C:20]([NH:23][NH2:24])([NH2:22])=[NH:21].[ClH:25].Cl.O>C(O)C>[ClH:25].[NH:23]([N:24]=[C:10]1[CH2:9][CH:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[OH:1])[CH2:17][C:16]2[N:15]=[CH:14][CH:13]=[C:12]([CH3:18])[C:11]1=2)[C:20]([NH2:22])=[NH:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 183173867-(2-Hydroxyphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-oneHCID 178418668HCID 178418668, compound

Product 1

HCID 178428110HCID 178428110, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 7-(2-hydroxyphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (0.08 g), aminoguanidine hydrochloride (0.037 g), concentrated hydrochloric acid (0.048 ml), water (0.048 ml) and ethanol (10 ml) was refluxed for 4 hours and cooled. 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 resulting crystals were washed with ethanol, while heating, to give 5-guanidinoimino-7-(2-hydroxyphenyl)-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride (Compound 68) (0.09 g) as colorless crystals.

Workup

  1. temperaturewas refluxed for 4 hours
  2. temperaturecooled
  3. customUnder reduced pressure, the solvent was evaporated
  4. dissolutionthe residue was dissolved in water
  5. washThe solution was washed with ethyl acetate
  6. concentrationconcentrated under reduced pressure
  7. washThe resulting crystals were washed with ethanol
  8. temperaturewhile heating

Sources & evidence

ORD record
ord-c72d7318b24746e48dfcf46fa5c87691
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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