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

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	Ethylenediamine	HCID 3301	—
Reactant	Sodium Hydroxide	HCID 14798	—
Reactant	p-Toluenesulfonic acid monohydrate	HCID 521998	—
Reactant	6-Methoxy-1,2,3,4-tetrahydroquinolin-2-one	HCID 10888467	—
Product	7-Methoxy-1,2,4,5-tetrahydroimidazo[1,2-a]quinoline	HCID 22132912	12%

Reaction Conditions

Temperature	200 °C

Reaction Steps

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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06143767
Source dataset	uspto-grants-2000_11
ORD ID	ord-eb22db6bf0ca4404982d53072d097e6c
Source note	uspto-grants-2000_11