2-(Dimethylamino)ethanol → 5-(2-Dimethylamino-ethoxy)-2-nitro-phenylamine

HRID 1909008Notes

Reaction equation

HRID 1909008 reaction equation
F[C:2]1[CH:3]=[C:4]([C:6]([N+:9]([O-:11])=[O:10])=[CH:7][CH:8]=1)[NH2:5].[CH3:12][N:13]([CH3:17])[CH2:14][CH2:15][OH:16].[OH-].[K+]>C1(C)C=CC=CC=1.O>[CH3:12][N:13]([CH3:17])[CH2:14][CH2:15][O:16][C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[C:4]([NH2:5])[CH:3]=1

Participants

6

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 14797Potassium HydroxideHCID 753995-Fluoro-2-nitroaniline

Product 1

HCID 203767455-(2-Dimethylamino-ethoxy)-2-nitro-phenylamineYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

3-Fluoro-6-nitroaniline (0.7 g, 4.48 mmol) and N,N-dimethylethanolamine (1.34 mL, 13.45 mmol) were dissolved in toluene (5 mL). This solution was cooled at 0° C. and finely ground KOH (1.258 g, 22.4 mmol) was added to the stirring mixture. The reaction mixture was stirred for 16 hours at room temperature, diluted with H2O (30 mL) and then extracted with CHCl3 (3×25 mL). The combined organics were dried (Na2SO4), filtered and the solvent was removed in vacuo. Purification by SiO2 chromatography (0% to 10% 2.0M NH3 in MeOH/dichloromethane) gave 5-(2-dimethylamino-ethoxy)-2-nitro-phenylamine as a dark oil (0.665 g, 90%). MS(ESI) m/z 226.0 (M+H)+

Workup

  1. extractionextracted with CHCl3 (3×25 mL)
  2. dry with materialThe combined organics were dried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvent was removed in vacuo
  5. customPurification by SiO2 chromatography (0% to 10% 2.0M NH3 in MeOH/dichloromethane)

Sources & evidence

ORD record
ord-a30b3142357e4b5ab783a177a277fad8
Source dataset
uspto-grants-2013_12
Patent number
US08598217B2

Reaction notes

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