Water → Ethyl 3-[(3-nitroquinolin-4-yl)amino]butanoate

HRID 549130

Reaction equation

HRID 549130 reaction equation
C(N(CC)CC)C.Cl[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[CH:11][C:10]=1[N+:19]([O-:21])=[O:20].[NH2:22][CH:23]([CH3:30])[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].O>CN(C=O)C>[N+:19]([C:10]1[CH:11]=[N:12][C:13]2[C:18]([C:9]=1[NH:22][CH:23]([CH3:30])[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:17][CH:16]=[CH:15][CH:14]=2)([O-:21])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 98103Ethyl 3-aminobutyrateHCID 112758084-Chloro-3-nitroquinoline

Product 1

HCID 67157227Ethyl 3-[(3-nitroquinolin-4-yl)amino]butanoateYield 99.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (12.8 mL, 91.8 mmol) was added to a solution of 4-chloro-3-nitroquinoline (8.0 g, 38 mmol) in DMF (100 mL). The resulting solution was stirred for five minutes at room temperature, and then ethyl 3-aminobutyrate (6.2 mL, 42 mmol) was added. The reaction was stirred overnight at room temperature and poured into deionized water (320 mL). The mixture was extracted with ethyl acetate (1×125 mL and 2×100 mL). The combined extracts were washed with brine (3×120 mL), dried over magnesium sulfate, filtered through a layer of CELITE filter agent, concentrated under reduced pressure, and further dried under high vacuum to provide 11.5 g of ethyl 3-[(3-nitroquinolin-4-yl)amino]butanoate as a yellow solid.

Workup

  1. stirringThe reaction was stirred overnight at room temperature
  2. extractionThe mixture was extracted with ethyl acetate (1×125 mL and 2×100 mL)
  3. washThe combined extracts were washed with brine (3×120 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered through a layer of CELITE filter agent
  6. concentrationconcentrated under reduced pressure
  7. customfurther dried under high vacuum

Sources & evidence

ORD record
ord-93bf2f81a5c64e81a21c964b3a211bca
Source dataset
uspto-grants-2011_05
Patent number
US07943609B2

Linked notes

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