Ethanolamine → 5-Chloro-6-(2-hydroxyethylamino)nicotinonitrile

HRID 1631017Notes

Reaction equation

HRID 1631017 reaction equation
[Cl:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([CH:9]=1)[C:7]#[N:8].[CH2:11]([CH2:13][NH2:14])[OH:12]>O1CCOCC1.CC(OC)(C)C>[Cl:1][C:2]1[C:3]([NH:14][CH2:13][CH2:11][OH:12])=[N:4][CH:5]=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

5

Reactant 2

HCID 700EthanolamineHCID 128784645,6-Dichloropyridine-3-carbonitrile

Product 1

HCID 585542055-Chloro-6-(2-hydroxyethylamino)nicotinonitrileYield 89.3%

Reagents, catalysts & solvents 2

HCID 15413tert-Butyl methyl etherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5,6-dichloro-nicotinonitrile (Bionet GC-0755, 500 mg, 2.89 mmol) and ethanolamine (0.87 mL, 14.45 mmol) was prepared in anhydrous dioxane (5 mL) and heated at 80° C. for 24 hours. The reaction mixture was diluted with MTBE (50 mL) and washed with water (2×25 mL) and brine (25 ml). The aqueous layers were extracted with MTBE (50 mL). The organic layers were combined, dried (Na2SO4) and concentrated under reduced pressure to give the title compound as a white powder (510 mg, 89%). HPLC (Method A), Rt: 1.9 min (purity: 99.9%). UPLC/MS, M−(ESI): 196.0.

Workup

  1. washwashed with water (2×25 mL) and brine (25 ml)
  2. extractionThe aqueous layers were extracted with MTBE (50 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b11165d2daa7499a92542ae889486fb3
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

Loading…