O-Methylhydroxylamine hydrochloride → HCID 76609476, compound

HRID 2426350Notes

Reaction equation

HRID 2426350 reaction equation
Cl.[O:2]([NH2:4])[CH3:3].[CH3:5][CH:6]([CH3:23])[CH2:7][N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]=[CH:12][C:11]=2[N:10]=[C:9]1[CH:21]=O>CO>[CH3:3][O:2][N:4]=[CH:21][C:9]1[N:8]([CH2:7][CH:6]([CH3:23])[CH3:5])[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]=[CH:12][C:11]=2[N:10]=1

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 86051826HCID 86051826, compound

Product 1

HCID 76609476HCID 76609476, compoundYield 104%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methoxylamine hydrochloride (0.659 g, 7.90 mmol) was added to a stirred suspension of 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline-2-carbaldehyde (1.00 g, 3.95 mmol) in methanol (10 mL), and the reaction was stirred at room temperature overnight. The methanol was removed under reduced pressure, and the residue was diluted with saturated aqueous sodium bicarbonate (50 mL). The resulting mixture was extracted with dichloromethane (3×30 mL), and the combined extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 1.16 g of 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline-2-carbaldehyde O-methyloxime as a pale yellow oil that solidified upon standing.

Workup

  1. customThe methanol was removed under reduced pressure
  2. additionthe residue was diluted with saturated aqueous sodium bicarbonate (50 mL)
  3. extractionThe resulting mixture was extracted with dichloromethane (3×30 mL)
  4. dry with materialthe combined extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b112aa6a39cf48feaa50e4a4e63e18f1
Source dataset
uspto-grants-2011_06
Patent number
US07968563B2

Reaction notes

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