Hydrochloric Acid → HCID 178424177, compound

HRID 1700543Notes

Reaction equation

HRID 1700543 reaction equation
[CH3:1][C:2]1[C:10]2[C:9](=O)[CH2:8][CH:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])[CH2:6][C:5]=2[NH:4][N:3]=1.[C:19]([NH:22][NH2:23])([NH2:21])=[NH:20].[ClH:24].Cl.O>C(O)C>[ClH:24].[NH:22]([N:23]=[C:9]1[CH2:8][CH:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[CH2:6][C:5]2[NH:4][N:3]=[C:2]([CH3:1])[C:10]1=2)[C:19]([NH2:21])=[NH:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 178418668HCID 178418668, compoundHCID 178424178HCID 178424178, compound

Product 1

HCID 178424177HCID 178424177, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-methyl-6-(2-methylphenyl)-4,5,6,7-tetrahydroindazol-4-one (0.15 g), aminoguanidine hydrochloride (0.072 g), concentrated hydrochloric acid (0.062 ml), water (0.062 ml) and ethanol (30 ml) was stirred at 50° C. for 3 hours and at 80° C. for 1.5 hours. Under reduced pressure, the solvent was evaporated. To the residue was added water, and the mixture was washed with diethylether. To the aqueous layer was added sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure, and to the residue was added 1N hydrochloric acid (1.5 ml). Under reduced pressure, the solvent was evaporated, and the resulting crystals were recrystallized from ethanol to give 4-guanidinoimino-3-methyl-6-(2-methylphenyl)-4,5,6,7-tetrahydroindazole hydrochloride (Compound 20) (0.18 g) as colorless crystals.

Workup

  1. customUnder reduced pressure, the solvent was evaporated
  2. additionTo the residue was added water
  3. washthe mixture was washed with diethylether
  4. additionTo the aqueous layer was added sodium hydrogen carbonate solution
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with water and saturated brine
  7. dry with materialdried with magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. additionto the residue was added 1N hydrochloric acid (1.5 ml)
  10. customUnder reduced pressure, the solvent was evaporated
  11. customthe resulting crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-7d9d25714fb644ee8b1724422ff46f64
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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