O-Methylhydroxylamine hydrochloride → HCID 86612269, compound

HRID 1623211Notes

Reaction equation

HRID 1623211 reaction equation
Cl.[O:2]([NH2:4])[CH3:3].[Br:5][C:6]1[CH:7]=[CH:8][C:9]2[C:10]3[N:18]([CH2:19][CH2:20][CH2:21][CH:22]=O)[C:17]([CH2:24][CH2:25][CH3:26])=[N:16][C:11]=3[CH:12]=[N:13][C:14]=2[CH:15]=1>C(O)C>[CH3:3][O:2][N:4]=[CH:22][CH2:21][CH2:20][CH2:19][N:18]1[C:10]2[C:9]3[CH:8]=[CH:7][C:6]([Br:5])=[CH:15][C:14]=3[N:13]=[CH:12][C:11]=2[N:16]=[C:17]1[CH2:24][CH2:25][CH3:26]

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 86052969HCID 86052969, compound

Product 1

HCID 86612269HCID 86612269, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methoxylamine hydrochloride (11.86 g, 142.1 mmol) was added to a solution of 4-(7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyraldehyde (25.6 g, 71.0 mmol, prepared as described in Example 17 Parts A through D) in ethanol (200 mL). The reaction mixture was stirred at room temperature for 2 hours and then concentrated under reduced pressure. The residue was dissolved in water, neutralized with saturated sodium bicarbonate, and then extracted into dichloromethane. The extract was washed sequentially with saturated sodium bicarbonate and brine, dried over magnesium sulfate, and then concentrated under reduced pressure to provide 27.1 g of 4-(7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyraldehyde O-methyloxime.

Workup

  1. customprepared
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted into dichloromethane
  5. washThe extract was washed sequentially with saturated sodium bicarbonate and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-daaa838f675a4e29bef0232fcc3c22f3
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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