2-(Methylamino)ethanol → 2-(Methyl(4-nitrophenyl)amino)ethan-1-ol

HRID 2236708Notes

Reaction equation

HRID 2236708 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][NH:12][CH2:13][CH2:14][OH:15]>CN1CCCC1=O>[CH3:11][N:12]([CH2:13][CH2:14][OH:15])[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 9590p-Fluoronitrobenzene

Product 1

HCID 45470772-(Methyl(4-nitrophenyl)amino)ethan-1-olYield 79%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 4-fluoronitrobenzene (2.8 g, 20 mmol) and 2-(methylamino)ethanol (8.9 g, 120 mmol) in N-methylpyrrolidinone (80 mL) is heated for 19 hours in a 85° C. oil bath. After cooling to room temperature, the reaction mixture is partitioned between ethyl acetate and water. The organic phase is washed five times with water and with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to give 2-(methyl-4-nitroanilino)ethanol (3.1 g, 79%) as a yellow solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture is partitioned between ethyl acetate and water
  3. washThe organic phase is washed five times with water
  4. dry with materialwith saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-903de5cde6e44909ad3e029b0d06a946
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…