Ammonium Hydroxide → HCID 21075716, compound

tert-Butyl N-(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)carbamate (14.3 g, 41.8 mmol) was dissolved in 150 mL of 2 M HCl in EtOH, and the reaction mixture was heated to reflux for 3 h. The reaction mixture was cooled and concentrated under reduced pressure to give a brown solid. The brown solid was dissolved in 100 mL of H2O and treated with 100 mL of concentrated NH4OH solution. The basic, aqueous solution was then extracted with CH2Cl2 (4×). The combined organic layers were then washed with brine and dried over Na2SO4. The solution was filtered and concentrated under reduced pressure to give a brown foam. The foam was triturated with Et2O (150 mL) and filtered. The filtrate was concentrated to give 2-ethoxymethy-1H-imidazo[4,5-c]quinolin-1-amine (5.77 g) as a tan solid.

1. temperaturethe reaction mixture was heated
2. temperatureto reflux for 3 h
3. temperatureThe reaction mixture was cooled
4. concentrationconcentrated under reduced pressure
5. customto give a brown solid
6. extractionThe basic, aqueous solution was then extracted with CH2Cl2 (4×)
7. washThe combined organic layers were then washed with brine
8. dry with materialdried over Na2SO4
9. filtrationThe solution was filtered
10. concentrationconcentrated under reduced pressure
11. customto give a brown foam
12. customThe foam was triturated with Et2O (150 mL)
13. filtrationfiltered
14. concentrationThe filtrate was concentrated

ORD record

ord-6d7735c0163046ba9f5182a3a4a7841b

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07163947B2