Hydrochloric Acid → 7-Methoxy-1,2,4,5-tetrahydroimidazo[1,2-a]quinoline

HRID 1740738Notes

Reaction equation

HRID 1740738 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=O)[CH2:7][CH2:6]2.[CH2:14](N)[CH2:15][NH2:16].CC1C=CC(S(O)(=O)=O)=CC=1.O.Cl.[OH-].[Na+]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]1[CH2:14][CH2:15][N:16]=[C:8]1[CH2:7][CH2:6]2

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 3301EthylenediamineHCID 14798Sodium HydroxideHCID 521998p-Toluenesulfonic acid monohydrateHCID 108884676-Methoxy-1,2,3,4-tetrahydroquinolin-2-one

Product 1

HCID 221329127-Methoxy-1,2,4,5-tetrahydroimidazo[1,2-a]quinolineYield 12%

Conditions

Temperature
200 °C

Procedure

To a mixture of Compound 13 (0.50 g, 2.6 mmol) and ethylenediamine (0.88 ml, 13.1 mmol) was added p-TsOH.H2O (2.5 g, 13.1 mmol), and heated to 200° C. for 24 h. The cooled mixture was solved with 6N HCl, basified with NaOH aq., and extracted with CH2Cl2. The organic layers were combined, dried over MgSO4, filtered, and concentrated. This residue was purified by SiO2 chromatography to give Compound 14 (63 mg, 0.31 mmol, 12%) as a colorless oil.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThis residue was purified by SiO2 chromatography

Sources & evidence

ORD record
ord-fa07752f04e44026ba5d17102c460989
Source dataset
uspto-grants-1999_10
Patent number
US05972930

Reaction notes

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