Hydrochloric Acid → HCID 178428159, compound

HRID 1700615Notes

Reaction equation

HRID 1700615 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]1[CH2:15][C:14]2[N:13]=[CH:12][CH:11]=[C:10]([CH3:16])[C:9]=2[C:8](=O)[CH2:7]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:29][NH:30][C:31]([NH:33][OH:34])=[NH:32].[ClH:35]>C(O)C>[ClH:35].[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]1[CH2:15][C:14]2[N:13]=[CH:12][CH:11]=[C:10]([CH3:16])[C:9]=2[C:8](=[N:29][NH:30][C:31](=[NH:32])[NH:33][OH:34])[CH2:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 109552977-(2-Furyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-oneHCID 178427660HCID 178427660, compound

Product 1

HCID 178428159HCID 178428159, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 7-(2-furyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (227 mg), 1-amino-3-hydroxyguanidine p-toluenesulfonate (314 mg) and concentrated hydrochloric acid (0.1 ml) in ethanol (3 ml) was stirred at 90° C. (bath temperature) for 2 hours. The reaction solution was concentrated under reduced pressure, and to the residue were added ethyl acetate (30 ml), tetrahydrofuran (20 ml) and 0.2 N sodium hydroxide (20 ml). The mixture was shaken, and the separated upper layer was washed with 0.2 N sodium hydroxide (10 ml) and water (10 ml, thrice). To the upper layer was added 2 N hydrochloric acid (1 ml), and the mixture was concentrated under reduced pressure. The residue in ethanol (3 ml) was stirred at 90° C. (bath temperature) for 3 hours and cooled, and crystals precipitated while stirring was filtered, washed with ethanol and dried to give 7-(2-furyl)-5-(1-hydroxyguanidin-3-yl)imino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride (Compound 97) (154 mg) as pale yellow crystals.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionto the residue were added ethyl acetate (30 ml), tetrahydrofuran (20 ml) and 0.2 N sodium hydroxide (20 ml)
  3. stirringThe mixture was shaken
  4. washthe separated upper layer was washed with 0.2 N sodium hydroxide (10 ml) and water (10 ml, thrice)
  5. additionTo the upper layer was added 2 N hydrochloric acid (1 ml)
  6. concentrationthe mixture was concentrated under reduced pressure
  7. stirringThe residue in ethanol (3 ml) was stirred at 90° C. (bath temperature) for 3 hours
  8. temperaturecooled
  9. customcrystals precipitated
  10. stirringwhile stirring
  11. filtrationwas filtered
  12. washwashed with ethanol
  13. customdried

Sources & evidence

ORD record
ord-2ab8f643125245b3893abc2e9dada6f2
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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