Triethylamine → HCID 68873567, compound

HRID 2366625Notes

Reaction equation

HRID 2366625 reaction equation
C(=O)([O-])[O-].[K+].[K+].C(N(CC)CC)C.Cl[C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=[CH:17][C:16]=1[N+:25]([O-:27])=[O:26].Cl.[CH2:29]([O:31][C:32](=[O:36])[CH2:33][CH2:34][NH2:35])[CH3:30]>C(Cl)(Cl)Cl.O>[N+:25]([C:16]1[CH:17]=[N:18][C:19]2[C:24]([C:15]=1[NH:35][CH2:34][CH2:33][C:32]([O:31][CH2:29][CH3:30])=[O:36])=[CH:23][CH:22]=[CH:21][CH:20]=2)([O-:27])=[O:26]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 112758084-Chloro-3-nitroquinoline

Product 1

HCID 68873567HCID 68873567, compoundYield 65.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

Potassium carbonate (19.87 g, 143.8 mmol) and triethylamine (50.1 mL, 359 mmol) were sequentially added with stirring to a solution of 4-chloro-3-nitroquinoline (30.0 g, 144 mmol) in chloroform (200 mL). After 15 minutes, β-alanine ethyl ester hydrochloride (26.5 g, 173 mmol) was slowly added, and the reaction was stirred overnight at ambient temperature. Water (100 mL) was added, and the mixture was stirred for 15 minutes. The organic layer was separated, washed sequentially with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 27.4 g of ethyl N-(3-nitroquinolin-4-yl)-β-alaninate as a yellow solid, which was used without purification.

Workup

  1. stirringthe mixture was stirred for 15 minutes
  2. customThe organic layer was separated
  3. washwashed sequentially with saturated aqueous sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1b06704ed28e4fd9b211f4d76810e0cd
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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