1-Fluoro-2-nitrobenzene → N-(2-Morpholinoethyl)-4-nitroaniline

HRID 640985Notes

Reaction equation

HRID 640985 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[N:11]1([CH2:17][CH2:18][NH2:19])[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C(N(C(C)C)CC)(C)C>O1CCOCC1>[N:11]1([CH2:17][CH2:18][NH:19][C:6]2[CH:5]=[CH:4][C:3]([N+:8]([O-:10])=[O:9])=[CH:2][CH:7]=2)[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 738951-Fluoro-2-nitrobenzeneHCID 81531DiisopropylethylamineHCID 4082852-Morpholinoethylamine

Product 1

HCID 21975017N-(2-Morpholinoethyl)-4-nitroanilineYield 71.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 50 mL round bottom flask was dried in an oven overnight and cooled to room temperature under Ar(g). The flask was charged with fluoronitrobenzene (0.187 mL, 1.77 mmol), 2-Morpholin-4-yl-ethylamine (0.299 g, 2.30 mmol) and dioxane (9.0 mL). To the solution, diisopropyl ethyl amine (0.463 mL, 2.66 mmol) was added dropwise and allowed to stir at 105° C. for 48 h. The mixture was extracted with EtOAc (3×30 mL), and with brine (2×30 mL). The combined organic layers were then dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude mixture was then purified over silica (10% MeOH/90% CHCl3) affording (2-Morpholin-4-yl-ethyl)-(4-nitro-phenyl)-amine as a yellow solid (0.315 g, 1.26 mmol, 71% yield).

Workup

  1. customA 50 mL round bottom flask was dried in an oven overnight
  2. extractionThe mixture was extracted with EtOAc (3×30 mL)
  3. dry with materialThe combined organic layers were then dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude mixture was then purified over silica (10% MeOH/90% CHCl3)

Sources & evidence

ORD record
ord-4602fb7724de4319a1769bcef10258e2
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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