2-(Methylamino)ethanol → 2-[Methyl(3-methyl-4-nitrophenyl)amino]ethanol

HRID 402667Notes

Reaction equation

HRID 402667 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=1.[CH3:12][NH:13][CH2:14][CH2:15][OH:16].C(N(CC)CC)C>CN1CCCC1=O>[CH3:8][C:6]1[CH:7]=[C:2]([N:13]([CH2:14][CH2:15][OH:16])[CH3:12])[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 80162-(Methylamino)ethanolHCID 8471TriethylamineHCID 949565-Fluoro-2-nitrotoluene

Product 1

HCID 609808482-[Methyl(3-methyl-4-nitrophenyl)amino]ethanol

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 5-fluoro-2-nitrotoluene (1.5 g, 9.6 mmol), N-methylethanolamine (0.90 mL, 0.012 mol) and triethylamine (1.6 mL, 0.012 mol) in N-methyl-2-pyrrolidone (15 mL) was stirred at 60° C. for 12 h. Cooled to ambient temperature, the reaction mixture was poured into ice water, extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate and concentrated to afford 2-[(3-methyl-4-nitrophenyl)-N-methylamino]ethanol as solid (2.0 g, y. 98%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6f18eb1e62c8408bb43107710db34586
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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