O-Methylhydroxylamine hydrochloride → 1-tert-butoxy-2-methyl-1H-imidazo[4,5-c]quinoline

HRID 2105496Notes

Reaction equation

HRID 2105496 reaction equation
Cl.[C:2]([O:6][NH2:7])([CH3:5])([CH3:4])[CH3:3].Cl.CON.Cl[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][C:14]=1[NH:23][C:24](=O)[CH3:25]>>[C:2]([O:6][N:7]1[C:13]2[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N:16]=[CH:15][C:14]=2[N:23]=[C:24]1[CH3:25])([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 3

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 67506066HCID 67506066, compound

Product 1

HCID 675069361-tert-butoxy-2-methyl-1H-imidazo[4,5-c]quinolineYield 51.9%

Procedure

The method of Part B of Example 25 was followed using O-(tert-butyl)hydroxylamine hydrochloride (2.0 g, 16 mmol) in lieu of O-methylhydroxylamine hydrochloride to treat N-(4-chloroquinolin-3-yl)acetamide (3.2 g, 14.5 mmol) with the modification that the reaction was heated at reflux for three hours. Following the work-up procedure, the resulting blue oil was purified by column chromatography on silica gel (eluting with 5% methanol in dichloromethane containing 5 mL of aqueous ammonium hydroxide per liter of eluent) to provide 1.92 g of 1-tert-butoxy-2-methyl-1H-imidazo[4,5-c]quinoline as a blue oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for three hours
  3. customthe resulting blue oil was purified by column chromatography on silica gel (eluting with 5% methanol in dichloromethane containing 5 mL of aqueous ammonium hydroxide per liter of eluent)

Sources & evidence

ORD record
ord-e334018a21ed4642a842b0f168c26776
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

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