Ammonia → HCID 178508166, compound

HRID 388582Notes

Reaction equation

HRID 388582 reaction equation
[CH2:1]([N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]=[C:12](Cl)[C:11]=2[N:10]=[C:9]1[OH:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:23]>CO>[NH2:23][C:12]1[C:11]2[N:10]=[C:9]([OH:22])[N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:20]=2[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N:13]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 178517322HCID 178517322, compound

Product 1

HCID 178508166HCID 178508166, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
170 °C

Procedure

1-Benzyl-4-chloro-1H-imidazo[4,5-c]quinolin-2-ol (approximately 1.1 g) and ammonia (approximately 100 mL of a 7 N solution in methanol) were added to a high-pressure vessel, which was sealed and heated in an oven at 170° C. for five days. The resulting solution was concentrated under reduced pressure, and the residue was purified by automated flash chromatography (silica cartridge, eluting with aqueous ammonium hydroxide:methanol:dichloromethane in a gradient from 0:0:100 to 0.2:4.8:95). A solid was present on top of the column; the solid was collected, washed with acetonitrile (6×100 mL), and purified again by automated flash chromatography (silica cartridge, eluting with aqueous ammonium hydroxide:methanol:dichloromethane in a gradient from 0.2:4.8:95 to 1:19:80) to provide 70 mg of 4-amino-1-benzyl-1H-imidazo[4,5-c]quinolin-2-ol as a white solid, mp greater than 250° C.

Workup

  1. customwhich was sealed
  2. concentrationThe resulting solution was concentrated under reduced pressure
  3. customthe residue was purified by automated flash chromatography (silica cartridge
  4. washeluting with aqueous ammonium hydroxide
  5. customthe solid was collected
  6. washwashed with acetonitrile (6×100 mL)
  7. custompurified again by automated flash chromatography (silica cartridge
  8. washeluting with aqueous ammonium hydroxide

Sources & evidence

ORD record
ord-78e83771fafe450c8a75594823d8292f
Source dataset
uspto-grants-2013_02
Patent number
US08377957B2

Reaction notes

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