Ethanolamine → 2-(2-Hydroxyethylamino)-1-(4-nitrophenyl)ethanol

HRID 387229

Reaction equation

HRID 387229 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:12][O:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:13]([CH2:15][NH2:16])[OH:14]>>[OH:14][CH2:13][CH2:15][NH:16][CH2:12][CH:10]([C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[OH:11]

Participants

3

Reactant 2

HCID 700EthanolamineHCID 922282-(4-Nitrophenyl)oxirane

Product 1

HCID 671197212-(2-Hydroxyethylamino)-1-(4-nitrophenyl)ethanolYield 60%

Conditions

Temperature
40 °C

Procedure

The mixture of 2-(4-nitro-phenyl)-oxirane (24.1 g, 0.15 mol) in ethanolamine (500 mL) was stirred at 40° C. for 2 h, then room temperature for 18 h. The reaction was partitioned between ethyl acetate (200 mL) and water (200 mL) and the aqueous layer was extracted with ethyl acetate (4×100 mL). The combined organic layers were dried over sodium sulfate, filtered and evaporated. The residue was triturated with acetonitrile and collected to give the title compound (19.80 g, 0.09 mmol, 60%) as a white solid. ESMS m/z 227 (M+H)+;

Workup

  1. waitroom temperature for 18 h
  2. customThe reaction was partitioned between ethyl acetate (200 mL) and water (200 mL)
  3. extractionthe aqueous layer was extracted with ethyl acetate (4×100 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was triturated with acetonitrile
  8. customcollected

Sources & evidence

ORD record
ord-8d11bdcb02f448218f1a3e5efe0cc5e6
Source dataset
uspto-grants-2013_02
Patent number
US08372970B2

Linked notes

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