2-(Methylamino)ethanol → 2-((4-Methoxy-3-nitrobenzyl)(methyl)amino)ethanol

HRID 42269Notes

Reaction equation

HRID 42269 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[C:5]([N+:11]([O-:13])=[O:12])[CH:4]=1.C(N(CC)CC)C.[CH3:21][NH:22][CH2:23][CH2:24][OH:25]>C(#N)C>[CH3:10][O:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][N:22]([CH3:21])[CH2:23][CH2:24][OH:25])=[CH:4][C:5]=1[N+:11]([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 80162-(Methylamino)ethanolHCID 8471TriethylamineHCID 115796484-(Bromomethyl)-1-methoxy-2-nitrobenzene

Product 1

HCID 609682012-((4-Methoxy-3-nitrobenzyl)(methyl)amino)ethanol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 5 mL round bottom flask was charged with 4-(bromomethyl)-1-methoxy-2-nitrobenzene (0.6 g, 2.44 mmol) and acetonitrile (2 mL). The solution was treated with triethylamine (1 mL, 7.32 mmol) and 2-(methylamino)ethanol (0.585 mL, 7.32 mmol), and the reaction was stirred at ambient temperature for 16 hours. The reaction was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated to provide the title compound. MS (DCI+) m/e 241.1 (M+H)+.

Workup

  1. customThe reaction was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ce71b24d047f4be5b9d6e493b0d3be4c
Source dataset
uspto-grants-2013_09
Patent number
US08536180B2

Reaction notes

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