Ethanol → HCID 57447047, compound

HRID 2366652Notes

Reaction equation

HRID 2366652 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH2:20]([O:22][CH2:23][C:24](Cl)=O)[CH3:21].C(N(CC)CC)C.C(O)C>ClCCl>[CH2:20]([O:22][CH2:23][C:24]1[N:12]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=1)[CH3:21]

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 84189Ethoxyacetyl chlorideHCID 68874499HCID 68874499, compound

Product 1

HCID 57447047HCID 57447047, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl N-(3-aminoquinolin-4-yl)-β-alaninate (20.0 g, 77.3 mmol, prepared in Parts A and B of Example 22) was treated with ethoxyacetyl chloride (11.29 g, 92.5 mmol) according to a modification the method described in Part A of Example 12. The reaction in dichloromethane (300 mL) was stirred for 1.5 hours, and after the addition of triethylamine (43.08 mL, 309.1 mmol) and ethanol (300 mL), the reaction was heated at reflux for four hours and then subjected to the work-up procedure to provide 25.0 g of ethyl 3-(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)propanoate.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for four hours

Sources & evidence

ORD record
ord-0585b1bb3c0e416d8911098d3cc5a057
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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