Sodium Hydroxide → HCID 86052868, compound

HRID 1623111Notes

Reaction equation

HRID 1623111 reaction equation
Cl.[O:2]([NH2:4])[CH3:3].[CH2:5]([C:8]1[N:9]([CH2:21][CH2:22][CH2:23][CH:24]=O)[C:10]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]=[CH:12][C:11]=2[N:20]=1)[CH2:6][CH3:7].[OH-].[Na+]>C(O)C.O>[CH3:3][O:2][N:4]=[CH:24][CH2:23][CH2:22][CH2:21][N:9]1[C:10]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]=[CH:12][C:11]=2[N:20]=[C:8]1[CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 521874O-Methylhydroxylamine hydrochlorideHCID 57464096HCID 57464096, compound

Product 1

HCID 86052868HCID 86052868, compoundYield 105.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Methoxylamine hydrochloride (3.37 g, 40.3 mmol) was added to a stirred solution of 4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyraldehyde (10.0 g, 35.5 mmol) in ethanol (100 mL) cooled to 0° C., followed by addition of 50% sodium hydroxide solution (12.5 M, 3.2 mL, 40 mmol) in water (7 mL). The reaction mixture was allowed to warm to ambient temperature and stirred for 3 days. The reaction mixture was then concentrated under reduce pressure and diluted with dichloromethane (150 mL) and water (50 mL). The layers were separated and the aqueous layer was extracted with dichloromethane (50 mL). The combined organics were dried over potassium carbonate, filtered and concentrated to afford 11.6 g of 4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-butyraldehyde O-methyloxime as a reddish oil.

Workup

  1. temperatureto warm to ambient temperature
  2. concentrationThe reaction mixture was then concentrated
  3. additiondiluted with dichloromethane (150 mL) and water (50 mL)
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with dichloromethane (50 mL)
  6. dry with materialThe combined organics were dried over potassium carbonate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0d4b39251499429a9d393c95681f06f3
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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