2-(Methylamino)ethanol → HCID 59418670, compound

HRID 1896585Notes

Reaction equation

HRID 1896585 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-74171bbb37e94b52809d0ac2811825e1
Source dataset
uspto-grants-2013_08
Patent number
US08518970B2

Reaction notes

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