Triethylamine → HCID 57447005, compound

HRID 2366585Notes

Reaction equation

HRID 2366585 reaction equation
C(N(CC)CC)C.C(=O)([O-])[O-].[K+].[K+].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.[NH2:29][CH2:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34]>O1CCCC1.C(Cl)(Cl)Cl>[N+:25]([C:16]1[CH:17]=[N:18][C:19]2[C:24]([C:15]=1[NH:29][CH2:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:23][CH:22]=[CH:21][CH:20]=2)([O-:27])=[O:26]

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 11430Potassium CarbonateHCID 112758084-Chloro-3-nitroquinoline2×HCID 126496614-Aminobutyrate ethyl hydrochloride2×

Product 1

HCID 57447005HCID 57447005, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (50.0 mL, 358 mmol) and potassium carbonate (40 g, 290 mmol) were added to a solution of 4-chloro-3-nitroquinoline (49.6 g, 238 mmol) in tetrahydrofuran (THF) (100 mL) and chloroform (250 mL). Ethyl 4-aminobutyrate hydrochloride (43.8 g, 262 mmol) was added in portions over a period of five minutes during which time an ice bath was used to cool the reaction. The reaction was stirred with cooling for 30 minutes, allowed to warm to ambient temperature, and stirred overnight. An analysis by thin layer chromatography (TLC) indicated the presence of 4-chloro-3-nitroquinoline. Additional ethyl 4-aminobutyrate hydrochloride (8.0 g, 48 mmol) was added, and the reaction was stirred at ambient temperature for one hour and then heated at reflux for two hours. Additional triethylamine (20 mL) was added, and the reaction was heated at reflux for one hour, cooled to ambient temperature, washed with water (3×100 mL), dried over potassium carbonate, filtered, and concentrated under reduced pressure to provide 63.8 g of ethyl 4-(3-nitroquinolin-4-ylamino)butyrate as a yellow solid.

Workup

  1. temperatureto cool
  2. customthe reaction
  3. temperaturewith cooling for 30 minutes
  4. stirringstirred overnight
  5. stirringthe reaction was stirred at ambient temperature for one hour
  6. temperatureheated
  7. temperatureat reflux for two hours
  8. temperaturethe reaction was heated
  9. temperatureat reflux for one hour
  10. temperaturecooled to ambient temperature
  11. washwashed with water (3×100 mL)
  12. dry with materialdried over potassium carbonate
  13. filtrationfiltered
  14. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-70455d85ab0b40cfa28a0d4f16d647cb
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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