Hydrochloric Acid → 4-Guanidinoimino-6-(2-hydroxyphenyl)-3-methyl-4,5,6,7-tetrahydroindazole hydrochloride

HRID 1700550Notes

Reaction equation

HRID 1700550 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:16][C:15]2[NH:14][N:13]=[C:12]([CH3:17])[C:11]=2[C:10](=O)[CH2:9]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:10]1[CH2:9][CH:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[OH:1])[CH2:16][C:15]2[NH:14][N:13]=[C:12]([CH3:17])[C:11]1=2)[C:19]([NH2:21])=[NH:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 178418668HCID 178418668, compoundHCID 178434191HCID 178434191, compound

Product 1

HCID 1784341824-Guanidinoimino-6-(2-hydroxyphenyl)-3-methyl-4,5,6,7-tetrahydroindazole hydrochlorideYield 108.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-(2-hydroxyphenyl)-3-methyl-4,5,6,7-tetrahydroindazol-4-one (0.04 g), aminoguanidine hydrochloride (0.02 g), concentrated hydrochloric acid (0.041 ml), water (0.041 ml) and ethanol (10 ml) was refluxed for 3 hours. Under reduced pressure, the solvent was evaporated. To the residue was added water, and the mixture was washed with ethyl acetate. Under reduced pressure, the solvent was evaporated, and the resulting crystals were recrystallized from ethanol to give 4-guanidinoimino-6-(2-hydroxyphenyl)-3-methyl-4,5,6,7-tetrahydroindazole hydrochloride (Compound 26) (0.06 g) as colorless crystals.

Workup

  1. temperaturewas refluxed for 3 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 resulting crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-51477241b5de40708c000086df070c5c
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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