Hydrochloric Acid → HCID 178428155, compound

HRID 1700624Notes

Reaction equation

HRID 1700624 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]=[CH:14][CH:13]=[C:12]([CH3:18])[C:11]=2[C:10](=O)[CH2:9]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:31][NH:32][C:33]([NH:35][OH:36])=[NH:34].Cl>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]=[CH:14][CH:13]=[C:12]([CH3:18])[C:11]=2[C:10](=[N:31][NH:32][C:33](=[NH:34])[NH:35][OH:36])[CH2:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 110655617-(2-Chlorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-oneHCID 178427660HCID 178427660, compound

Product 1

HCID 178428155HCID 178428155, compoundYield 166.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 7-(2-chlorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (679 mg), 1-amino-3-hydroxyguanidine p-toluenesulfonate (917 mg) and concentrated hydrochloric acid (0.3 ml) in ethanol (10 ml) was stirred at 90° C. (bath temperature) for 3 hours. The reaction solution was concentrated under reduced pressure, and to the residue were added ethyl acetate (40 ml), tetrahydrofuran (30 ml) and 0.2 N sodium hydroxide (50 ml). The mixture was shaken, and the separated upper layer was washed with 0.2 N sodium hydroxide (20 ml) and water (15 ml, thrice). To the upper layer was added 2 N hydrochloric acid (2.5 ml), and the mixture was concentrated under reduced pressure. To the residue was added ethanol (10 ml), and the mixture was stirred at 900° C. (bath temperature) for 3 hours and cooled to give crystals, which were filtered to give 7-(2-chlorophenyl)-5-(1-hydroxyguanidin-3-yl)imino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride (Compound 106) (790 mg) as pale yellow crystals.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionto the residue were added ethyl acetate (40 ml), tetrahydrofuran (30 ml) and 0.2 N sodium hydroxide (50 ml)
  3. stirringThe mixture was shaken
  4. washthe separated upper layer was washed with 0.2 N sodium hydroxide (20 ml) and water (15 ml, thrice)
  5. additionTo the upper layer was added 2 N hydrochloric acid (2.5 ml)
  6. concentrationthe mixture was concentrated under reduced pressure
  7. additionTo the residue was added ethanol (10 ml)
  8. stirringthe mixture was stirred at 900° C. (bath temperature) for 3 hours
  9. temperaturecooled
  10. customto give crystals, which
  11. filtrationwere filtered

Sources & evidence

ORD record
ord-1ef4315738c2463c9fac14a417302a6e
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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