Ethanolamine → HCID 59026691, compound

HRID 1924030Notes

Reaction equation

HRID 1924030 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1O)=[N:11][CH:10]=[CH:9][CH:8]=2)([O-:3])=[O:2].[CH2:15]([CH2:17][NH2:18])[OH:16].O>C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:18][CH2:17][CH2:15][OH:16])=[N:11][CH:10]=[CH:9][CH:8]=2)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 962WaterHCID 178526774HCID 178526774, compound

Product 1

HCID 59026691HCID 59026691, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-nitro[1,5]naphthyridin-4-ol (9.14 g, 43.7 mmol) dissolved in 300 mL of CH2Cl2 was treated with ethanolamine (7.9 mL, 130 mmol) and the mixture was stirred under N2. After 3 hours, the reaction mixture was concentrated to give a yellow solid. The yellow solid was treated with 200 mL of H2O and the suspension was heated to reflux, with stirring, for 10 minutes. The mixture was cooled in an ice bath. The resulting yellow solid was isolated by filtration, washed with cold H2O and dried with suction to give 2-[(3-nitro[1,5]naphthyridin-4-yl)amino]ethanol (10.02 g) as fine yellow crystals.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customto give a yellow solid
  3. temperaturethe suspension was heated
  4. temperatureto reflux
  5. stirringwith stirring, for 10 minutes
  6. temperatureThe mixture was cooled in an ice bath
  7. customThe resulting yellow solid was isolated by filtration
  8. washwashed with cold H2O
  9. customdried with suction

Sources & evidence

ORD record
ord-ef30d69a350e455fb12f19b2db642f43
Source dataset
uspto-grants-2012_05
Patent number
US08178539B2

Reaction notes

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