Hydrochloric Acid → 2-(4-chloro-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)ethylamine

HRID 606067Notes

Reaction equation

HRID 606067 reaction equation
[Cl:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:25][O:26][CH2:27][CH3:28])[N:14]([CH2:15][CH2:16][NH:17]C(=O)OC(C)(C)C)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.Cl.[OH-].[Na+]>O1CCOCC1>[Cl:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:25][O:26][CH2:27][CH3:28])[N:14]([CH2:15][CH2:16][NH2:17])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86616884tert-butyl 2-(4-chloro-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl]ethylcarbamate

Product 1

HCID 862476222-(4-chloro-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)ethylamineYield 65.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl 2-(4-chloro-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl]ethylcarbamate (1.55 g, 3.83 mmol) in a solution of 4 M hydrogen chloride in dioxane (15 mL) was stirred at room temperature for two hours. An aqueous solution of 2 M sodium hydroxide was added to adjust the reaction to pH 13. The solution was extracted with several portions of dichloromethane. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated. The crude product was purified by flash chromatography (silica gel, gradient elution from 97:3 to 97:5 dichloromethane/methanol) to afford 2-(4-chloro-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)ethylamine (760 mg) as a white solid.

Workup

  1. customthe reaction to pH 13
  2. extractionThe solution was extracted with several portions of dichloromethane
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography (silica gel, gradient elution from 97:3 to 97:5 dichloromethane/methanol)

Sources & evidence

ORD record
ord-04d400383bf946d8a1a63712fa27747f
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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