Hydrochloric Acid → HCID 178423835, compound

HRID 1700616Notes

Reaction equation

HRID 1700616 reaction equation
[CH3:1][C:2]1[C:11]2[C:10](=O)[CH2:9][CH:8]([C:13]3[S:14][C:15]([CH3:18])=[CH:16][CH:17]=3)[CH2:7][C:6]=2[N:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:30][NH:31][C:32]([NH:34][OH:35])=[NH:33].[ClH:36]>C(O)C>[ClH:36].[OH:35][NH:34][C:32]([NH:31][N:30]=[C:10]1[CH2:9][CH:8]([C:13]2[S:14][C:15]([CH3:18])=[CH:16][CH:17]=2)[CH2:7][C:6]2[N:5]=[CH:4][CH:3]=[C:2]([CH3:1])[C:11]1=2)=[NH:33]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 18317648HCID 18317648, compoundHCID 178427660HCID 178427660, compound

Product 1

HCID 178423835HCID 178423835, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-methyl-7-(5-methyl-2-thienyl)-5,6,7,8-tetrahydroquinolin-5-one (257 mg), 1-amino-3-hydroxyguanidine p-toluenesulfonate (285 mg) and concentrated hydrochloric acid (0.2 ml) in ethanol (3 ml) was stirred at 90° C. (bath temperature) for 1 hour. 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 (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 in ethanol (1 ml) was stirred at room temperature for 15 hours to give crystals, which were filtered and dried to give 5-(1-hydroxyguanidin-3-yl)imino-4-methyl-7-(5-methyl-2-thienyl)-5,6,7,8-tetrahydroquinoline hydrochloride (Compound 98) (163 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 (10 ml) and water (10 ml, thrice)
  5. additionTo the upper layer was added 2 N hydrochloric acid (1 ml)
  6. concentrationthe mixture was concentrated under reduced pressure
  7. stirringThe residue in ethanol (1 ml) was stirred at room temperature for 15 hours
  8. customto give crystals, which
  9. filtrationwere filtered
  10. customdried

Sources & evidence

ORD record
ord-2913caf2c72f448ca55bf8dff2fcfdd1
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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