Hydrochloric Acid → HCID 178428165, compound

HRID 1700622Notes

Reaction equation

HRID 1700622 reaction equation
[Cl:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH:7]1[CH2:16][C:15]2[N:14]=[CH:13][CH:12]=[C:11]([CH3:17])[C:10]=2[C:9](=O)[CH2:8]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:30][NH:31][C:32]([NH:34][OH:35])=[NH:33].Cl>C(O)C>[ClH:1].[Cl:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH:7]1[CH2:16][C:15]2[N:14]=[CH:13][CH:12]=[C:11]([CH3:17])[C:10]=2[C:9](=[N:30][NH:31][C:32](=[NH:33])[NH:34][OH:35])[CH2:8]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10891160HCID 10891160, compoundHCID 178427660HCID 178427660, compound

Product 1

HCID 178428165HCID 178428165, compoundYield 118.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 7-(2-chlorothiophen-3-yl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (222 mg), 1-amino-3-hydroxyguanidine p-toluenesulfonate (314 mg) and concentrated hydrochloric acid (0.1 ml) in ethanol (4 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 (15 ml) and water (10 ml, thrice). To the upper layer was added 2 N hydrochloric acid (0.8 ml), and the mixture was concentrated under reduced pressure. To the residue was added ether (3 ml), and the mixture was stirred at 90° C. (bath temperature) for 3 hours and cooled to give crystals, which were filtered, washed with ethanol and dried to give 7-(2-chlorothiophen-3-yl)-5-(1-hydroxyguanidin-3-yl)imino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride (Compound 104) (183 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 (15 ml) and water (10 ml, thrice)
  5. additionTo the upper layer was added 2 N hydrochloric acid (0.8 ml)
  6. concentrationthe mixture was concentrated under reduced pressure
  7. additionTo the residue was added ether (3 ml)
  8. stirringthe mixture was stirred at 90° C. (bath temperature) for 3 hours
  9. temperaturecooled
  10. customto give crystals, which
  11. filtrationwere filtered
  12. washwashed with ethanol
  13. customdried

Sources & evidence

ORD record
ord-48d157ef6ccf4777be06fd1d68adad97
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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