Hydrochloric Acid → HCID 178494713, compound

HRID 1700735Notes

Reaction equation

HRID 1700735 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]([CH2:17][O:18][CH3:19])[C:11]=2[C:10](=O)[CH2:9]1.[C:21]([NH:24][NH2:25])([NH2:23])=[NH:22].Cl.Cl.O>C(O)C>[ClH:1].[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]([CH2:17][O:18][CH3:19])[C:11]=2[C:10](=[N:25][NH:24][C:21]([NH2:23])=[NH:22])[CH2:9]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 183176226-(2-Chlorophenyl)-3-methoxymethyl-4,5,6,7-tetrahydroindazol-4-oneHCID 178418668HCID 178418668, compound

Product 1

HCID 178494713HCID 178494713, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-(2-chlorophenyl)-3-methoxymethyl-4,5,6,7-tetrahydroindazol-4-one (0.1 g), aminoguanidine hydrochloride (0.046 g), concentrated hydrochloric acid (0.086 ml), water (0.086 ml) and ethanol (10 ml) was refluxed for 5 hours. Under reduced pressure, the solvent was evaporated, and to the residue was added sodium hydrogen carbonate solution to make the solution alkaline. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and concentrated under reduced pressure. The residue was dissolved in 1N hydrochloric acid (1ml), and the solution was concentrated. The resulting crystals were recrystallized from ethanol-ethyl acetate to give 6-(2-chlorophenyl)-4-guanidinoimino-3-methoxymethyl-4,5,6,7-tetrahydroindazole hydrochloride (Compound 148) (0.06 g) as colorless crystals.

Workup

  1. temperaturewas refluxed for 5 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
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in 1N hydrochloric acid (1ml)
  8. concentrationthe solution was concentrated
  9. customThe resulting crystals were recrystallized from ethanol-ethyl acetate

Sources & evidence

ORD record
ord-b27811c90a39471daaf3c9691ae743c6
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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