Hydrochloric Acid → HCID 178434177, compound

HRID 1700545Notes

Reaction equation

HRID 1700545 reaction equation
[Cl: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].Cl.Cl.O>C(O)C>[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[Cl: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 1784341903-Methyl-6-(2-chlorophenyl)-4,5,6,7-tetrahydroindazol-4-one

Product 1

HCID 178434177HCID 178434177, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-(2-chlorophenyl)-3-methyl-4,5,6,7-tetrahydroindazol-4-one (1.05 g), aminoguanidine hydrochloride (0.47 g), concentrated hydrochloric acid (0.44 ml), water (0.44 ml) and ethanol (70 ml) was refluxed for 6 hours. Under reduced pressure, the solvent was evaporated, and to the residue was added sodium hydrogen carbonate solution. The mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated to give 4-guanidinoimino-6-(2-chlorophenyl)-3-methyl-4,5,6,7-tetrahydroindazole (0.6 g) as amorphous. To a solution of 4-guanidinoimino-6-(2-chlorophenyl)-3-methyl-4,5,6,7-tetrahydroindazole (0.3 g) in ethanol (10 ml) was added methanesulfonic acid (0.18 g), and the mixture was concentrated. The resulting crystals were recrystallized from water-ethanol to give 4-guanidinoimino-6-(2-chlorophenyl)-3-methyl-4,5,6,7-tetrahydroindazole methanesulfonate (Compound 22) (0.28 g).

Workup

  1. temperaturewas refluxed for 6 hours
  2. customUnder reduced pressure, the solvent was evaporated
  3. additionto the residue was added sodium hydrogen carbonate solution
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried with magnesium sulfate
  7. customUnder reduced pressure, the solvent was evaporated

Sources & evidence

ORD record
ord-f795d2474f2848a69836d944ded62e81
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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