2-(Methylamino)ethanol → HCID 19915726, compound

HRID 1032665Notes

Reaction equation

HRID 1032665 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([CH2:8][CH2:9]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:13][NH:14][CH2:15][CH2:16][OH:17]>C1(C)C(C)=CC=CC=1>[CH3:13][N:14]([CH2:15][CH2:16][OH:17])[CH2:9][CH2:8][C:7]1[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 792664-Nitrophenethyl bromide

Product 1

HCID 19915726HCID 19915726, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 4-nitrophenethyl bromide (11.5 g) and N-methylethanolamine (8.25 g) in xylene (100 ml) was stirred at reflux for 16 hours. After evaporation, the residue was partitioned between 5% aqueous sodium bicarbonate and methylene chloride. The organic liquors were washed with saturated aqueous brine, dried (MgSO4), filtered and evaporated to give an orange oil (10.1 g). Chromatography on silica ("Kieselgel 60"-Trade Mark) eluting with ethyl acetate followed by collection and evaporation of suitable fractions gave the title compound as a yellow oil, (7.5 g).

Workup

  1. temperatureat reflux for 16 hours
  2. customAfter evaporation
  3. customthe residue was partitioned between 5% aqueous sodium bicarbonate and methylene chloride
  4. washThe organic liquors were washed with saturated aqueous brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-3920e4e69caf42fea22a6aef27f5a98c
Source dataset
uspto-grants-1990_09
Patent number
US04959366

Reaction notes

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