Ethanol → HCID 57447013, compound

HRID 2366594Notes

Reaction equation

HRID 2366594 reaction equation
[CH2:1]([O:3][CH2:4][C:5](Cl)=O)[CH3:2].[NH2:8][C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[NH:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:16][CH:15]=[CH:14][CH:13]=2.C(N(CC)CC)C.C(O)C>ClCCl>[CH2:1]([O:3][CH2:4][C:5]1[N:19]([CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:8]=1)[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 84189Ethoxyacetyl chlorideHCID 57447009HCID 57447009, compound

Product 1

HCID 57447013HCID 57447013, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of ethoxyacetyl chloride (6.61 g, 54.0 mmol) in dichloromethane (10 mL) was added dropwise to a solution of ethyl 4-[(3-aminoquinolin-4-yl)amino]butanoate (11.8 g, 43.2 mmol) in dichloromethane (150 mL). The reaction was stirred for 30 minutes and then concentrated under reduced pressure. Triethylamine (16.7 g, 165 mmol) and ethanol (150 mL) were added, and the resulting solution was heated at reflux for four hours. The solvent was removed under reduced pressure. Dichloromethane (75 mL) was added, and the resulting solution was washed sequentially with water (3×75 mL) and saturated aqueous sodium bicarbonate (75 mL), dried over potassium carbonate, filtered, and concentrated under reduced pressure to provide 12.5 g of ethyl 4-[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butanoate as a dark oil.

Workup

  1. concentrationconcentrated under reduced pressure
  2. temperaturethe resulting solution was heated
  3. temperatureat reflux for four hours
  4. customThe solvent was removed under reduced pressure
  5. additionDichloromethane (75 mL) was added
  6. washthe resulting solution was washed sequentially with water (3×75 mL) and saturated aqueous sodium bicarbonate (75 mL)
  7. dry with materialdried over potassium carbonate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-20b14f24b3cf41ea9f4ef682020dbc61
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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