2-(Methylamino)ethanol → HCID 59418670, compound

HRID 1641071Notes

Reaction equation

HRID 1641071 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[CH3:12][NH:13][CH2:14][CH2:15][OH:16].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:13]([CH3:12])[CH2:14][CH2:15][OH:16])=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

6

Reactant 3

HCID 80162-(Methylamino)ethanolHCID 11430Potassium CarbonateHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Product 1

HCID 59418670HCID 59418670, compoundYield 111.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

5-bromo-2-fluoronitrobenzene (5.0 g, 22.7 mmol), 2-(methylamino)ethanol (4.26 g, 56.8 mmol) and K2CO3 (9.4 g, 68.1 mmol) in DMF (20 mL) was heated to 60° C. for 1.5 hours, cooled to rt, diluted with water and extracted with EtOAc. The organic phases were washed with water, brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to provide 6.98 g (100%) of the desired product 2-((4-bromo-2-nitrophenyl)(methyl)amino)ethanol (25B): 1H NMR (300 MHz, CDCl3) δ 7.87 (1H, d), 7.51 (1H, dd), 7.10 (1H, d), 3.77 (2H, t), 3.39 (2H, t), 2.83 (3H, s).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phases were washed with water, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5904dc3f598b47f690e540110081465c
Source dataset
uspto-grants-2012_02
Patent number
US08114893B2

Reaction notes

Loading…