Ammonia → HCID 178508170, compound

HRID 388616Notes

Reaction equation

HRID 388616 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:25]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:18]=[C:17](Cl)[C:16]=2[N:15]=[C:14]1[OH:27])(C(C)(C)C)(C)C.[NH3:28]>CO>[NH2:28][C:17]1[C:16]2[N:15]=[C:14]([OH:27])[N:13]([CH2:12][CH2:11][CH2:10][CH2:9][OH:8])[C:25]=2[C:24]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N:18]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 178455216HCID 178455216, compound

Product 1

HCID 178508170HCID 178508170, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

1-[4-(tert-Butyldimethylsilanyloxy)butyl]-4-chloro-1H-imidazo[4,5-c]quinolin-2-ol (5.0 g, 12 mmol) and ammonia (200 mL of a 7 N solution in methanol) were added to a high-pressure vessel, which was sealed and heated in an oven at 150° C. for five days, allowed to cool, and concentrated under reduced pressure. The crude product was triturated with hexane for 15 minutes, and the resulting solid was isolated by filtration, washed with hexane (500 mL), and dried under vacuum to provide 3.53 g of 4-amino-1-(4-hydroxybutyl)-1H-imidazo[4,5-c]quinolin-2-ol as a light gray solid.

Workup

  1. customwhich was sealed
  2. temperatureto cool
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was triturated with hexane for 15 minutes
  5. customthe resulting solid was isolated by filtration
  6. washwashed with hexane (500 mL)
  7. customdried under vacuum

Sources & evidence

ORD record
ord-0794f5e19dc34465b4c1fd33f406e10c
Source dataset
uspto-grants-2013_02
Patent number
US08377957B2

Reaction notes

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