Hydrochloric Acid → 8-(2-aminoethoxy)-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine

HRID 2203494Notes

Reaction equation

HRID 2203494 reaction equation
Cl.[NH2:2][C:3]1[C:12]2[N:13]=[C:14]([CH2:19][O:20][CH2:21][CH3:22])[N:15]([CH2:16][CH2:17][CH3:18])[C:11]=2[C:10]2[CH:9]=[C:8]([O:23][CH2:24][CH2:25][NH:26]C(=O)OC(C)(C)C)[CH:7]=[CH:6][C:5]=2[N:4]=1>C(O)C>[NH2:26][CH2:25][CH2:24][O:23][C:8]1[CH:7]=[CH:6][C:5]2[N:4]=[C:3]([NH2:2])[C:12]3[N:13]=[C:14]([CH2:19][O:20][CH2:21][CH3:22])[N:15]([CH2:16][CH2:17][CH3:18])[C:11]=3[C:10]=2[CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68974513tert-butyl 2-[(4-amino-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl)oxy]ethylcarbamate

Product 1

HCID 588336918-(2-aminoethoxy)-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-4-amineYield 85.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of hydrogen chloride (55 mL of 1.2 M) in ethanol was added to tert-butyl 2-[(4-amino-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl)oxy]ethylcarbamate (3.98 g, 8.97 mmol), and the reaction was heated at reflux for one hour. The reaction mixture was allowed to cool to ambient temperature, and the solvent was removed under reduced pressure. The resulting yellow solid was dissolved in a small volume of water, and 10% aqueous sodium hydroxide was added to adjust to pH 13. The mixture was then extracted with dichloromethane (3×100 mL), and the combined extracts were washed sequentially with water and brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting solid was recrystallized from acetonitrile to provide 2.63 g of 8-(2-aminoethoxy)-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine as fine, peach-colored needles, mp 157-159° C.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for one hour
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe resulting yellow solid was dissolved in a small volume of water, and 10% aqueous sodium hydroxide
  5. additionwas added
  6. extractionThe mixture was then extracted with dichloromethane (3×100 mL)
  7. washthe combined extracts were washed sequentially with water and brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe resulting solid was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-c6eaee18750c4d44beadfc2ffed4112c
Source dataset
uspto-grants-2016_06
Patent number
US09365567B2

Reaction notes

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