Hydrochloric Acid → 4-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butylamine

HRID 9388Notes

Reaction equation

HRID 9388 reaction equation
Cl.C(OC(=O)[NH:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:25]2[C:24]3[CH:23]=[CH:22][C:21]([Br:26])=[CH:20][C:19]=3[N:18]=[CH:17][C:16]=2[N:15]=[C:14]1[CH2:27][O:28][CH2:29][CH3:30])(C)(C)C>C(O)C>[Br:26][C:21]1[CH:22]=[CH:23][C:24]2[C:25]3[N:13]([CH2:12][CH2:11][CH2:10][CH2:9][NH2:8])[C:14]([CH2:27][O:28][CH2:29][CH3:30])=[N:15][C:16]=3[CH:17]=[N:18][C:19]=2[CH:20]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86593758tert-butyl[4-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]carbamate

Product 1

HCID 219843404-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butylamineYield 93.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Concentrated hydrochloric acid (15.6 mL, 0.194 mol) was added to a solution of tert-butyl[4-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]carbamate (23.2 g, 48 mmol) in ethanol, and the reaction was heated at reflux for 20 minutes. A precipitate formed, and the reaction was allowed to cool to ambient temperature overnight. The solid was isolated by filtration, washed with ethanol, and dissolved in water. The solution was washed with dichloromethane and then made basic with the addition of 50% aqueous sodium hydroxide. The basic solution was extracted with dichloromethane (3×300 mL), and the combined extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 17 g of 4-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butylamine as an off-white solid.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 20 minutes
  3. customA precipitate formed
  4. customThe solid was isolated by filtration
  5. washwashed with ethanol
  6. dissolutiondissolved in water
  7. washThe solution was washed with dichloromethane
  8. additionmade basic with the addition of 50% aqueous sodium hydroxide
  9. extractionThe basic solution was extracted with dichloromethane (3×300 mL)
  10. dry with materialthe combined extracts were dried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7fc97130c44c4ab6862ae4441f6c5ab3
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Reaction notes

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