Ammonia → HCID 178467391, compound

HRID 388620Notes

Reaction equation

HRID 388620 reaction equation
Cl[C:2]1[C:11]2[N:12]=[C:13]([O:15][CH2:16][CH3:17])[NH:14][C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[NH3:18]>CO>[CH2:16]([O:15][C:13]1[NH:14][C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([NH2:18])[C:11]=2[N:12]=1)[CH3:17]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 178467387HCID 178467387, compound

Product 1

HCID 178467391HCID 178467391, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

4-Chloro-2-ethoxy-1H-imidazo[4,5-c]quinoline (500 mg) was added to a high-pressure vessel with ammonia (40 mL of a 7 N solution in methanol), and the vessel was sealed and heated at 150° C. overnight. An analysis by LC/MS indicated the presence of starting material, and the reaction was heated at 150° C. for an additional four hours, allowed to cool, and concentrated under reduced pressure. The crude product was purified twice by automated flash chromatography (silica cartridge, eluting with aqueous ammonium hydroxide:methanol:dichloromethane in a gradient from 0:0:100 to 0.4:7.6:92) to provide 52 mg of 2-ethoxy-1H-imidazo[4,5-c]quinolin-4-amine as a white solid.

Workup

  1. customwas sealed
  2. temperaturethe reaction was heated at 150° C. for an additional four hours
  3. temperatureto cool
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified twice by automated flash chromatography (silica cartridge
  6. washeluting with aqueous ammonium hydroxide

Sources & evidence

ORD record
ord-0d0f31d161534541a223c5ceba111061
Source dataset
uspto-grants-2013_02
Patent number
US08377957B2

Reaction notes

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