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

HRID 1856775Notes

Reaction equation

HRID 1856775 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-eb22db6bf0ca4404982d53072d097e6c
Source dataset
uspto-grants-2000_11
Patent number
US06143767

Reaction notes

Loading…