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

HRID 2105483Notes

Reaction equation

HRID 2105483 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[NH:12][CH:13]=O.Cl.[C:16]([O:20][NH2:21])([CH3:19])([CH3:18])[CH3:17]>>[C:16]([O:20][N:21]1[C:2]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[N:5]=[CH:4][C:3]=2[N:12]=[CH:13]1)([CH3:19])([CH3:18])[CH3:17]

Participants

3

Reactant 2

HCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 86227468N-(4-chloroquinolin-3-yl)formamide

Product 1

HCID 675060801-tert-butoxy-1H-imidazo[4,5-c]quinolineYield 70.5%

Procedure

4-Chloroquinolin-3-ylformamide (4.1 g, 0.020 mol) was treated with O-(tert-butyl)hydroxylamine hydrochloride (2.8 g, 22 mmol) according to the method of Part B of Example 20 to provide 3.4 g of 1-tert-butoxy-1H-imidazo[4,5-c]quinoline, which was used without chromatographic purification.

Sources & evidence

ORD record
ord-ebcb214f86f64e73b98249c24301ca6e
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

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