Hydrochloric Acid → HCID 178428156, compound

HRID 1700613Notes

Reaction equation

HRID 1700613 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[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].Cl>C(O)C>[ClH:1].[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[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 10957724HCID 10957724, compoundHCID 178427660HCID 178427660, compound

Product 1

HCID 178428156HCID 178428156, compoundYield 188.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 7-(2,3-dichlorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (306 mg), 1-amino-3-hydroxyguanidine p-toluenesulfonate (320 mg) and concentrated hydrochloric acid (0.2 ml) in ethanol (6 ml) was stirred at 85° C. (bath temperature) for 2 hours and 30 minutes. 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 (25 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 was recrystallized form ethanol and dried to give 7-(2,3-dichlorophenyl)-5-(1-hydroxyguanidin-3-yl)imino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride (Compound 95) (390 mg) as yellow crystals.

Workup

  1. custom30 minutes
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. additionto the residue were added ethyl acetate (30 ml), tetrahydrofuran (20 ml) and 0.2 N sodium hydroxide (25 ml)
  4. stirringThe mixture was shaken
  5. washthe separated upper layer was washed with 0.2 N sodium hydroxide (10 ml) and water (10 ml, thrice)
  6. additionTo the upper layer was added 2 N hydrochloric acid (1 ml)
  7. concentrationthe mixture was concentrated under reduced pressure
  8. customThe residue was recrystallized form ethanol
  9. customdried

Sources & evidence

ORD record
ord-f3d60c8c8fc14ce383c35f8a4018b104
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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