Ammonium Hydroxide → HCID 57447012, compound

HRID 2366592Notes

Reaction equation

HRID 2366592 reaction equation
[OH-].[NH4+:2].[CH2:3]([C:6]1[N:7]([CH2:19][CH2:20][CH2:21][C:22](OCC)=[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]>CC1CCCO1>[CH2:3]([C:6]1[N:7]([CH2:19][CH2:20][CH2:21][C:22]([NH2:2])=[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]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 57447006HCID 57447006, compound

Product 1

HCID 57447012HCID 57447012, compound

Reagents, catalysts & solvents 1

HCID 73012-MethyltetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

Concentrated ammonium hydroxide (8.0 mL of 29%) was added to a solution of ethyl 4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butanoate (5.1 g, 16 mmol) in 2-methyltetrahydrofuran (10 mL), and the mixture was heated overnight in a sealed high-pressure vessel at 80° C. An analysis by liquid chromatography/mass spectrometry (LC/MS) indicated the reaction was incomplete. The solvents were evaporated under a stream of nitrogen, and ammonium acetate (10 g) was added. The vessel was sealed and heated overnight at 135° C. The reaction was allowed to cool to ambient temperature, and water (50 mL) was added. The mixture was filtered, and the filtrate was washed with saturated aqueous sodium bicarbonate (25 mL), dried over potassium carbonate, filtered, and concentrated under reduced pressure to provide 2.95 g of 4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butanamide as a light brown solid.

Workup

  1. customThe solvents were evaporated under a stream of nitrogen, and ammonium acetate (10 g)
  2. additionwas added
  3. customThe vessel was sealed
  4. temperatureheated overnight at 135° C
  5. temperatureto cool to ambient temperature
  6. additionwater (50 mL) was added
  7. filtrationThe mixture was filtered
  8. washthe filtrate was washed with saturated aqueous sodium bicarbonate (25 mL)
  9. dry with materialdried over potassium carbonate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f9b40818b95f488082c8ce5c5045f710
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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