Triethylamine → Ethyl 5-(3-nitroquinolin-4-ylamino)pentanoate

HRID 2362570Notes

Reaction equation

HRID 2362570 reaction equation
C(=O)([O-])[O-].[K+].[K+].C(N(CC)CC)C.Cl.[NH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].Cl[C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]=[CH:28][C:27]=1[N+:36]([O-:38])=[O:37]>C(Cl)(Cl)Cl.O>[N+:36]([C:27]1[CH:28]=[N:29][C:30]2[C:35]([C:26]=1[NH:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:34][CH:33]=[CH:32][CH:31]=2)([O-:38])=[O:37]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 112758084-Chloro-3-nitroquinolineHCID 16094861Ethyl 5-aminopentanoate hydrochloride

Product 1

HCID 57447067Ethyl 5-(3-nitroquinolin-4-ylamino)pentanoateYield 101.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

Potassium carbonate (66.23 g, 0.479 mol), triethylamine (167 mL, 1.20 mol), and ethyl 5-aminovalerate hydrochloride (104 g, 0.575 mol) were added to a mixture of 4-chloro-3-nitroquinoline (100 g, 0.470 mol) in chloroform (1 L). The reaction mixture was stirred at room temperature for 4 hours, then water (200 mL) was added. The mixture was transferred to a separatory funnel and the layers were separated. The organic layer was washed with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford 151 g of ethyl 5-[(3-nitroquinolin-4-yl)amino]pentanoate.

Workup

  1. customThe mixture was transferred to a separatory funnel
  2. customthe layers were separated
  3. washThe organic layer was washed 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-3c64d3d5e6464d9baa5f3cff8c34ce25
Source dataset
uspto-grants-2014_04
Patent number
US08691837B2

Reaction notes

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