Ethanolamine → HCID 20280073, compound

HRID 1247924Notes

Reaction equation

HRID 1247924 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:8]([CH2:10][NH2:11])[OH:9]>O>[OH:9][CH2:8][CH2:10][NH:11][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 122863-Bromopyridine

Product 1

HCID 20280073HCID 20280073, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-bromopyridine (25.10 g), ethanolamine (34.89 g) and cupric sulfate (2.90 g) in water (140 ml) was refluxed for 5 hours under stirring. The reaction mixture was washed with chloroform and the aqueous layer was separated out. To the aqueous solution was added an aqueous solution of potassium carbonate (22 g) and then the mixture was saturated with sodium chloride, and extracted with a mixed solvent of chloroform and ethanol (1:1). The extract was evaporated and the residue was subjected to column chromatography on silica gel (200 g) using a mixed solvent of chloroform and ethanol (5:1) as an eluent. The fractions containing an object compound were collected and evaporated to give 3-(2-hydroxyethyl)aminopyridine (5.96 g) as an oil.

Workup

  1. temperaturewas refluxed for 5 hours
  2. washThe reaction mixture was washed with chloroform
  3. customthe aqueous layer was separated out
  4. additionTo the aqueous solution was added an aqueous solution of potassium carbonate (22 g)
  5. extractionextracted with a mixed solvent of chloroform and ethanol (1:1)
  6. customThe extract was evaporated
  7. additionThe fractions containing an object compound
  8. customwere collected
  9. customevaporated

Sources & evidence

ORD record
ord-4a05a6bce26944a283a42c3f6972c7d4
Source dataset
uspto-grants-1985_06
Patent number
US04521413

Reaction notes

Loading…