Sodium Bicarbonate → HCID 57455407, compound

HRID 1623196Notes

Reaction equation

HRID 1623196 reaction equation
[BH4-].[Na+].[CH2:3]([C:6]1[N:7]([CH2:19][CH2:20][CH2:21][CH:22]=[O:23])[C:8]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:18]=1)[CH2:4][CH3:5].C(=O)(O)[O-].[Na+]>C(O)C>[CH2:3]([C:6]1[N:7]([CH2:19][CH2:20][CH2:21][CH2:22][OH:23])[C:8]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:18]=1)[CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 57464096HCID 57464096, compound

Product 1

HCID 57455407HCID 57455407, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (2.28 g, 60.4 mmol) was added to a solution of 4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyraldehyde (prepared as described in Parts A-C of Example 6, 17.0 g, 60.4 mmol) in ethanol (200 mL). The reaction mixture was stirred for 2 hours, then saturated aqueous sodium bicarbonate was added. The ethanol was removed under reduced pressure and the mixture was extracted with dichloromethane. The organic layer was washed with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield 15.7 g of 4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butan-1-ol as a yellow oil.

Workup

  1. customThe ethanol was removed under reduced pressure
  2. extractionthe mixture was extracted with dichloromethane
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8ddcc8726df74614884555ae392f2ebd
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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