O-Methylhydroxylamine hydrochloride → HCID 67505818, compound

HRID 2105497Notes

Reaction equation

HRID 2105497 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][C:13](=O)[CH3:14].Cl.[O:17]([CH2:24][CH2:25][O:26][NH2:27])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl.CON>>[CH3:14][C:13]1[N:27]([O:26][CH2:25][CH2:24][O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[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]=1

Participants

4

Reactant 3

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 12604316O-(2-Phenoxyethyl)hydroxylamine--hydrogen chloride (1/1)HCID 67506066HCID 67506066, compound

Product 1

HCID 67505818HCID 67505818, compoundYield 65%

Procedure

The method of Part B of Example 25 was used to treat N-(4-chloroquinolin-3-yl)acetamide (2.9 g, 13 mmol) with O-(2-phenoxyethyl)hydroxylamine hydrochloride (2.5 g, 13 mmol) in lieu of O-methylhydroxylamine hydrochloride with the modification that the reaction was heated at reflux overnight. 2-Methyl-1-(2-phenoxyethoxy)-1H-imidazo[4,5-c]quinoline (2.7 g) was obtained as a dark oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight

Sources & evidence

ORD record
ord-104069db4cdc41eab34decdc00af5be0
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

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