Triethylamine → Tert-butyl methyl(2-(2-[(3-nitroquinolin-4-yl)amino]ethoxy}ethyl)carbamate

HRID 1839002Notes

Reaction equation

HRID 1839002 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].C(N(CC)CC)C.[NH2:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][N:28]([CH3:36])[C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32]>C(Cl)Cl>[CH3:36][N:28]([CH2:27][CH2:26][O:25][CH2:24][CH2:23][NH:22][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13])[C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:32])[CH3:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 112758084-Chloro-3-nitroquinolineHCID 85823338tert-butyl N-(2-(2-aminoethoxy)ethyl)-N-methylcarbamate

Product 1

HCID 69010146Tert-butyl methyl(2-(2-[(3-nitroquinolin-4-yl)amino]ethoxy}ethyl)carbamateYield 77.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 4-chloro-3-nitroquinoline (32.3 g, 155 mmol) in 400 mL of anhydrous CH2Cl2, under N2, was treated with triethylamine (43.1 mL, 310 mmol) and tert-butyl 2-(2-aminoethoxy)ethyl(methyl)carbamate (37.2 g, 171 mmol). After stirring overnight, the reaction mixture was washed with H2O (2×300 mL) and brine (300 mL). The organic portion was dried over Na2SO4 and concentrated to give a brown oil. Column chromatography (SiO2, 33% ethyl acetate/hexanes-67% ethyl acetate/hexanes) gave 46.7 g of tert-butyl methyl(2-{2-[(3-nitroquinolin-4-yl)amino]ethoxy}ethyl)carbamate as a yellow solid.

Workup

  1. washthe reaction mixture was washed with H2O (2×300 mL) and brine (300 mL)
  2. dry with materialThe organic portion was dried over Na2SO4
  3. concentrationconcentrated
  4. customto give a brown oil

Sources & evidence

ORD record
ord-8c7eaa74b2a647aaa61fbbe3b4d30928
Source dataset
uspto-grants-2004_01
Patent number
US06677347B2

Reaction notes

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