Diethyl Ether → HCID 21075819, compound

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.

1. concentrationthe reaction mixture was concentrated under reduced pressure
2. customto give a brown solid
3. temperaturethe mixture was refluxed overnight
4. concentrationThe reaction mixture was concentrated under reduced pressure
5. customto give a dark-red oil
6. washwashed with H2O (2×75 mL) and brine (75 mL)
7. dry with materialThe organic portion was dried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customto give a red solid
11. filtrationfiltered
12. customto remove insoluble material
13. concentrationThe filtrate was concentrated

ORD record

ord-c787c3304f6a4c3aa632149fdc354750

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07163947B2