Hydrochloric Acid → HCID 178424849, compound

HRID 1700612Notes

Reaction equation

HRID 1700612 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH:9]1[CH2:18][C:17]2[N:16]=[CH:15][CH:14]=[C:13]([CH3:19])[C:12]=2[C:11](=O)[CH2:10]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:32][NH:33][C:34]([NH:36][OH:37])=[NH:35].[ClH:38]>C(O)C>[ClH:38].[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH:9]1[CH2:18][C:17]2[N:16]=[CH:15][CH:14]=[C:13]([CH3:19])[C:12]=2[C:11](=[N:32][NH:33][C:34](=[NH:35])[NH:36][OH:37])[CH2:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 183173177-(2,5-Dimethylphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-oneHCID 178427660HCID 178427660, compound

Product 1

HCID 178424849HCID 178424849, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 7-(2,5-dimethylphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (100 mg), 1-amino-3-hydroxyguanidine p-toluenesulfonate (131 mg) and concentrated hydrochloric acid (0.1 ml) in ethanol (2 ml) was stirred at 85° C. (bath temperature) for 1 hour. The reaction solution was concentrated under reduced pressure, and to the residue were added ethyl acetate (20 ml), tetrahydrofuran (12 ml) and 0.2 N sodium hydroxide (10 ml). The mixture was shaken, and the separated upper layer was washed with 0.2 N sodium hydroxide (5 ml) and water (5 ml, thrice). To the upper layer was added 2 N hydrochloric acid (0.5 ml), and the mixture was concentrated under reduced pressure. The residue was washed with a mixture of ether (4 ml) and ethanol (2 ml), and dried to give 7-(2,5-dimethylphenyl)-5-(1-hydroxyguanidin-3-yl)imino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride (Compound 94) (121 mg) as yellow crystals.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionto the residue were added ethyl acetate (20 ml), tetrahydrofuran (12 ml) and 0.2 N sodium hydroxide (10 ml)
  3. stirringThe mixture was shaken
  4. washthe separated upper layer was washed with 0.2 N sodium hydroxide (5 ml) and water (5 ml, thrice)
  5. additionTo the upper layer was added 2 N hydrochloric acid (0.5 ml)
  6. concentrationthe mixture was concentrated under reduced pressure
  7. washThe residue was washed with a mixture of ether (4 ml) and ethanol (2 ml)
  8. customdried

Sources & evidence

ORD record
ord-6d8274606346441b94a6eb5ed7eadfb0
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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