Sodium Bicarbonate → HCID 57447110, compound

HRID 2366719Notes

Reaction equation

HRID 2366719 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[NH:12][C:13](=O)[CH2:14][CH2:15][CH3:16].Cl.[CH2:19]([O:21][C:22](=[O:25])[CH2:23][NH2:24])[CH3:20].C(=O)(O)[O-].[Na+]>ClCCl>[CH2:14]([C:13]1[N:24]([CH2:23][C:22]([O:21][CH2:19][CH3:20])=[O:25])[C:2]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[N:5]=[CH:4][C:3]=2[N:12]=1)[CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2723640Glycine ethyl ester, hydrochlorideHCID 57447109HCID 57447109, compound

Product 1

HCID 57447110HCID 57447110, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A neat mixture of N-(4-chloroquinolin-3-yl)butanamide (5.0 g, 20 mmol) and glycine ethyl ester hydrochloride (10.0 g, 72 mmol) was heated gently with a heat gun until the solids melted. The reaction was followed by LC/MS, and heat was applied briefly twice more until no starting material remained. Dichloromethane (100 mL) and saturated aqueous sodium bicarbonate (50 mL) were added, and the resulting mixture was stirred until all solids were dissolved. The aqueous layer was separated and extracted with dichloromethane (2×50 mL), and the combined organic fractions were washed sequentially with saturated aqueous sodium bicarbonate (50 mL) and water, dried over potassium carbonate, filtered, and concentrated under reduced pressure. The residue was (3.6 g) was dissolved in hot toluene (150 mL), and pyridinium tosylate (100 mg) was added. The reaction was heated at reflux under a Dean-Stark trap for one hour, allowed to stand at ambient temperature for three days, heated at reflux for two hours, cooled to ambient temperature, and diluted with dichloromethane (150 mL). The resulting solution was washed with saturated aqueous sodium bicarbonate (2×35 mL), dried over potassium carbonate, filtered, and concentrated under reduced pressure to provide 3.2 g of ethyl (2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)acetate as a light brown solid.

Workup

  1. temperaturewas heated gently with a heat gun until the solids
  2. temperatureheat
  3. dissolutionwere dissolved
  4. customThe aqueous layer was separated
  5. extractionextracted with dichloromethane (2×50 mL)
  6. washthe combined organic fractions were washed sequentially with saturated aqueous sodium bicarbonate (50 mL) and water
  7. dry with materialdried over potassium carbonate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. dissolutionwas dissolved in hot toluene (150 mL)
  11. additionpyridinium tosylate (100 mg) was added
  12. temperatureThe reaction was heated
  13. temperatureat reflux under a Dean-Stark trap for one hour
  14. temperatureheated
  15. temperatureat reflux for two hours
  16. additiondiluted with dichloromethane (150 mL)
  17. washThe resulting solution was washed with saturated aqueous sodium bicarbonate (2×35 mL)
  18. dry with materialdried over potassium carbonate
  19. filtrationfiltered
  20. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8edff745224f4cc68435fbf3af50df31
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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