Diethyl Ether → HCID 21075819, compound

Participants

Reaction Steps

A solution of tert-butyl N′-(3-aminoquinolin-4-yl)hydrazinecarboxylate (12.15 g, 44.3 mmol) in 200 mL of anhydrous CH2Cl2 was cooled to 0° C. and treated with triethylamine (7.72 mL, 55.4 mmol) and 2-ethoxyacetyl chloride (5.70 g, 46.5 mmol) under an atmosphere of N2. After 3 h, an additional 1 mL of 2-ethoxyacetyl chloride was added. After stirring for 2 h, the reaction mixture was concentrated under reduced pressure to give a brown solid. This was dissolved in 150 mL of EtOH and treated with 18.5 mL of triethylamine, and the mixture was refluxed overnight. The reaction mixture was concentrated under reduced pressure to give a dark-red oil. The red oil was dissolved in 200 mL of CH2Cl2 and washed with H2O (2×75 mL) and brine (75 mL). The organic portion was dried over Na2SO4, filtered, and concentrated under reduced pressure to give a red solid. The solid was treated with a minimum amount of hot Et2O and filtered to remove insoluble material. The filtrate was concentrated to give tert-butyl N-(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)carbamate (14.3 g) as a tan solid.

Provenance & Evidence