Hydrochloric Acid → 7-(2-Chlorophenyl)-5-guanidinoimino-4-methyl-1,2,5,6,7,8-hexahydroquinolin-2-one hydrochloride

HRID 1700679Notes

Reaction equation

HRID 1700679 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[NH:15][C:14](=[O:18])[CH:13]=[C:12]([CH3:19])[C:11]=2[C:10](=O)[CH2:9]1.[C:21]([NH:24][NH2:25])([NH2:23])=[NH:22].Cl.C(OCCO)C.Cl>>[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[NH:15][C:14](=[O:18])[CH:13]=[C:12]([CH3:19])[C:11]=2[C:10](=[N:25][NH:24][C:21]([NH2:23])=[NH:22])[CH2:9]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8076Glycol monoethyl etherHCID 18317534HCID 18317534, compoundHCID 178418668HCID 178418668, compound

Product 1

HCID 1784295427-(2-Chlorophenyl)-5-guanidinoimino-4-methyl-1,2,5,6,7,8-hexahydroquinolin-2-one hydrochlorideYield 157.6%

Conditions

Temperature
135 °C

Procedure

To a mixture of 7-(2-chlorophenyl)-4-methyl-1,2,5,6,7,8-hexahydroquinoline-2,5-dione (0.144 g) and aminoguanidine hydrochloride (61 mg) were added 2-ethoxyethanol (2.5 ml) and concentrated hydrochloric acid (0.1 ml), and the mixture was stirred at 135° C. for 1 hour and cooled. Precipitated crystals were filtered, washed with methanol and dried to give 7-(2-chlorophenyl)-5-guanidinoimino-4-methyl-1,2,5,6,7,8-hexahydroquinolin-2-one hydrochloride (Compound 139) (0.15 g) as colorless crystals.

Workup

  1. temperaturecooled
  2. customPrecipitated crystals
  3. filtrationwere filtered
  4. washwashed with methanol
  5. customdried

Sources & evidence

ORD record
ord-6799f6422dd146a8b27613a20483cb19
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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