Hydrochloric Acid → HCID 178428160, compound

HRID 1700614Notes

Reaction equation

HRID 1700614 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[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].Cl>C(O)C>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[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 110012577-(2,6-Dichlorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-oneHCID 178427660HCID 178427660, compound

Product 1

HCID 178428160HCID 178428160, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 7-(2,6-dichlorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (153 mg), 1-amino-3-hydroxyguanidine p-toluenesulfonate (262 mg) and concentrated hydrochloric acid (0.1 ml) in ethanol (3 ml) was stirred at 90° C. (bath temperature) for 1.5 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 (15 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 (0.5 ml), and the mixture was concentrated under reduced pressure. The residue was washed with a mixture of ether (3 ml) and ethanol (1.5 ml) and dried to give 7-(2,6-dichlorophenyl)-5-(1-hydroxyguanidin-3-yl)imino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride (Compound 96) 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 (15 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 (0.5 ml)
  6. concentrationthe mixture was concentrated under reduced pressure
  7. washThe residue was washed with a mixture of ether (3 ml) and ethanol (1.5 ml)
  8. customdried

Sources & evidence

ORD record
ord-0339d7586cff4b1ea550047c02006054
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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