Hydrochloric Acid → 5-Guanidinoimino-4-methyl-7-(3-thienyl)-5,6,7,8-tetrahydroquinoline hydrochloride

HRID 1700618Notes

Reaction equation

HRID 1700618 reaction equation
[CH3:1][C:2]1[C:11]2[C:10](=O)[CH2:9][CH:8]([C:13]3[CH:17]=[CH:16][S:15][CH:14]=3)[CH2:7][C:6]=2[N:5]=[CH:4][CH:3]=1.[C:18]([NH:21][NH2:22])([NH2:20])=[NH:19].[ClH:23].Cl>C(O)C>[ClH:23].[NH:21]([N:22]=[C:10]1[CH2:9][CH:8]([C:13]2[CH:17]=[CH:16][S:15][CH:14]=2)[CH2:7][C:6]2[N:5]=[CH:4][CH:3]=[C:2]([CH3:1])[C:11]1=2)[C:18]([NH2:20])=[NH:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 117706614-Methyl-7-(3-thienyl)-5,6,7,8-tetrahydroquinolin-5-oneHCID 178418668HCID 178418668, compound

Product 1

HCID 1784281455-Guanidinoimino-4-methyl-7-(3-thienyl)-5,6,7,8-tetrahydroquinoline hydrochlorideYield 107.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-methyl-7-(3-thienyl)-5,6,7,8-tetrahydroquinolin-5-one (243 mg), aminoguanidine hydrochloride (122 mg) and concentrated hydrochloric acid (0.2 ml) in ethanol (3 ml) was refluxed for 2 hours. The reaction solution was cooled, and precipitated crystals were filtered, washed with ethanol and dried to give 5-guanidinoimino-4-methyl-7-(3-thienyl)-5,6,7,8-tetrahydroquinoline hydrochloride (Compound 100) (362 mg) as colorless crystals.

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperatureThe reaction solution was cooled
  3. customprecipitated crystals
  4. filtrationwere filtered
  5. washwashed with ethanol
  6. customdried

Sources & evidence

ORD record
ord-f48e5abe54a6469b82b66bf0a0669253
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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