Sodium Bicarbonate → HCID 57447024, compound

HRID 2366607Notes

Reaction equation

HRID 2366607 reaction equation
C([O-])(=O)C.[NH4+:5].[CH2:6]([C:9]1[N:10]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29]CC)=O)[C:11]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[CH:13][C:12]=2[N:21]=1)[CH2:7][CH3:8].C(=O)(O)[O-].[Na+]>>[CH2:6]([C:9]1[N:10]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([NH2:5])=[O:29])[C:11]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[CH:13][C:12]=2[N:21]=1)[CH2:7][CH3:8]

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 517165Ammonium AcetateHCID 57447018HCID 57447018, compound

Product 1

HCID 57447024HCID 57447024, compoundYield 45.2%

Procedure

Ammonium acetate (20 g) and ethyl 6-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)hexanoate (4.11 g, 11.6 mmol) were heated overnight at 140° C. in a sealed vessel. The reaction was allowed to cool to ambient temperature, and saturated aqueous sodium bicarbonate was added. The mixture was extracted with chloroform (3×), and the extracts were combined and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (eluting with 95:5 dichloromethane:methanol) to provide 1.7 g of 6-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)hexanamide.

Workup

  1. extractionThe mixture was extracted with chloroform (3×)
  2. concentrationconcentrated under reduced pressure
  3. customThe crude product was purified by column chromatography on silica gel (eluting with 95:5 dichloromethane:methanol)

Sources & evidence

ORD record
ord-f172a7948fe642e09c42d207ef9ba850
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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