Acetone → HCID 58835277, compound

HRID 1992599Notes

Reaction equation

HRID 1992599 reaction equation
[NH2:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[C:10]([NH2:19])[C:9]=2[N:8]=[C:7]1[CH2:20][CH2:21][CH3:22].[CH3:23][C:24]([CH3:26])=O>CO>[NH2:19][C:10]1[C:9]2[N:8]=[C:7]([CH2:20][CH2:21][CH3:22])[N:6]([CH2:5][CH2:4][CH2:3][O:2][N:1]=[C:24]([CH3:26])[CH3:23])[C:18]=2[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:11]=1

Participants

4

Reactant 2

HCID 180AcetoneHCID 114494201H-Imidazo[4,5-c]quinolin-4-amine, 1-[3-(aminooxy)propyl]-2-propyl-

Product 1

HCID 58835277HCID 58835277, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-[3-(aminooxy)propyl]-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine (prepared as described in Example 1, 0.605 g, 2.02 mmol) in methanol was heated until the starting material dissolved. Acetone (3 mL, 40 mmol) was then added, and the resulting solution was stirred for two hours. The reaction was then concentrated under reduced pressure, and the residue (800 mg) was purified by column chromatography on silica gel (25 g, eluting sequentially with 98:2 dichloromethane:methanol and 95:5 dichloromethane:methanol) to provide 600 mg of acetone O-[3-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]oxime as a beige powder, mp 147-150° C.

Workup

  1. temperaturewas heated until the starting material
  2. dissolutiondissolved
  3. concentrationThe reaction was then concentrated under reduced pressure
  4. customthe residue (800 mg) was purified by column chromatography on silica gel (25 g
  5. washeluting sequentially with 98:2 dichloromethane

Sources & evidence

ORD record
ord-77285aefa1de4bc1a496d3dc996c5bf4
Source dataset
uspto-grants-2010_01
Patent number
US07648997B2

Reaction notes

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