Hydrochloric Acid → HCID 178479521, compound

HRID 1700732Notes

Reaction equation

HRID 1700732 reaction equation
[Cl: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]=[N:14][CH:13]=[C:12]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[C:11]=2[C:10](=O)[CH2:9]1.[C:26]([NH:29][NH2:30])([NH2:28])=[NH:27].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[CH2:17][C:16]2[N:15]=[N:14][CH:13]=[C:12]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[C:11]=2[C:10](=[N:30][NH:29][C:26]([NH2:28])=[NH:27])[CH2:9]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 183175497-(2-Chlorophenyl)-4-(4-chlorophenyl)-5,6,7,8-tetrahydrocinnolin-5-oneHCID 178418668HCID 178418668, compound

Product 1

HCID 178479521HCID 178479521, compoundYield 115.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 7-(2-chlorophenyl)-4-(4-chlorophenyl)-5,6,7,8-tetrahydrocinnolin-5-one (0.18 g) and aminoguanidine hydrochloride (65 mg) in ethanol (10 ml) were added concentrated hydrochloric acid (0.12 ml) and water (0.12 ml), and the mixture was refluxed for 6 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 purified with silica gel column chromatography (ethyl acetate-methanol). The resulting crystals were dissolved in 1N hydrochloric acid (1 ml), and the solution was concentrated. The residue was recrystallized from ethanol-ethyl acetate to give 7-(2-chlorophenyl)-4-(4-chlorophenyl)-5-guanidinoimino-5,6,7,8-tetrahydrocinnoline hydrochloride (Compound 145) (0.13 g) as colorless crystals.

Workup

  1. temperaturethe mixture was 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
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified with silica gel column chromatography (ethyl acetate-methanol)
  8. dissolutionThe resulting crystals were dissolved in 1N hydrochloric acid (1 ml)
  9. concentrationthe solution was concentrated
  10. customThe residue was recrystallized from ethanol-ethyl acetate

Sources & evidence

ORD record
ord-8f23f9e5f8754cc18139853baad8967a
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

Loading…