Ethanolamine → 19298-14-7

HRID 433336Notes

Reaction equation

HRID 433336 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].F[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[OH:2][CH2:1][CH2:3][NH:4][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 9590p-FluoronitrobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 942988919298-14-7Yield 20%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of ethanolamine (2.29 g, 37.5 mmol) and 1-fluoro-4-nitrobenzene (3.53 g, 25.0 mmol) in dimethylsulphoxide (25 ml) was treated with potassium carbonate (6.9 g, 50 mmol) and heated at 90° C. overnight. The mixture was cooled and poured onto water (250 ml), the precipitated solid filtered off, dried, dissolved in ethanol (50 ml) and hydrogenated over 10% Pd/C for 4 h at ambient temperature . The catalyst was removed by filtration, the ethanol evaporated and the residue purified by column chromatography using EtOAc to yield the title compound (740 mg, 5.0 mmol). NMR: 2.95 (t, 2H), 3.5 (t, 2H), 4.1 (s, 2H), 4.4 (s, 1H), 4.55 (t, 1H), 6.4 (m, 4H); MS: 153 (M+H)+.

Workup

  1. temperatureThe mixture was cooled
  2. additionpoured onto water (250 ml)
  3. filtrationthe precipitated solid filtered off
  4. customdried
  5. dissolutiondissolved in ethanol (50 ml) and hydrogenated over 10% Pd/C for 4 h at ambient temperature
  6. customThe catalyst was removed by filtration
  7. customthe ethanol evaporated
  8. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-2bb57eda8f5444ccb8d7445c962547c7
Source dataset
uspto-grants-2003_12
Patent number
US06667342B1

Reaction notes

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